Antibacterial surface active agent containing azaalkenelactam

ABSTRACT

An antibacterial surface active agent comprising an effective amount of at least one cyclic amide represented by the general formula ##STR1## wherein R is an alkyl group, alkenyl group, alkylaryl group, alkylarylalkyl group, hydroxyalkyl group, acyl group or hydroxyl-substituted acyl group having 8 to 22 carbon atoms in total, R&#39;, R&#34; and R&#39;&#34; are hydrogen atoms or methyl groups, A is hydrogen atom or methyl group, 0≦W≦1, 0≦X+Z≦3, 0≦Y≦3, 0≦p+q+r≦3, m=1 or 2 and n=2 or 3; said compound may assume a structure in which, if necessary, the nitrogen atoms, except for the amide grouping, may combine with an organic acid radical by covalent bond or to add to an organic or inorganic acid.

TECHNICAL FIELD

This invention relates to novel antibacterial surface active agentscontaining novel cyclic amides. More particularly, the antibacterialsurface active agent of this invention comprises a compound which has inthe same molecule a hydrophobic group comprising a chain of 8 to 22carbon bonds and a hydrophilic group as shown below, comprising a 7- or8--membered lactam group containing a basic nitrogen atom, ##STR2##wherein R', R" and R'" are hydrogen atoms or methyl groups, m=1 or 2 andn=2 or 3; said compound may assume a structure which allows the compoundto combine at the position of said basic nitrogen atom with an organicacid radical by covalent bond or to add to an organic or inorganic acid.

DISCLOSURE OF THE INVENTION

As a result of extensive studies, the present inventors confirmed by IR,NMR and mass spectral analyses of the reaction products that on reactingan acetoacetic ester or formylpropionic ester of a lower alcohol with apolyamine having primary amino groups and secondary amino groups whichare interposed therebetween with 2 or 3 methylene radicals there isformed at first a nitrile bond by the reaction between said primaryamino group of the polyamine and the carbonyl group of the ketone oraldehyde, followed by the formation of a lactam group by the reactionbetween said secondary amino group and the carbonyl group of the esterin the same molecule; they further confirmed by neutralization titrationusing an organic and an inorganic acids that the nitrogen forming saidnitrile bond has a basic property, and found that the reaction productsincluding those having an organic acid radical obtained by the reactionof a monohalocarboxylic acid with said nitrogen have a surface activityat the liquid-water interfaces and have an antibacterial activity, too.

More particularly, the antibacterial surface active compound of thisinvention is a cyclic amide represented by the general formula ##STR3##(wherein, R is an alkyl group, alkenyl group, alkylaryl preferablymonoalkylphenyl group, alkylarylalkyl preferably monoalkylbenzyl group,hydroxyalkyl group, acyl preferably alkylcarbonyl or alkenylcarbonylgroup, or hydroxyl-substituted acyl preferably hydroxyl-substitutedalkycarbonyl or alkenylcarbonyl group having 8 to 22 total carbon atoms,R', R" and R'" are hydrogen atoms or methyl groups, A is hydrogen atomor hydroxyl group, O≦W≦1, O≦X+Z≦3, O≦Y≦3, O≦p+q+r≦3, m=1 or 2, and n=2or 3; said cyclic amide may have a structure which, if necessary, allowsthe nitrogen atoms, except for the amide group, to combine with anorganic acid radical by covalent bond or to add to an organic orinorganic acid) which is formed by reacting an acetoacetic ester orformylpropionic ester of an alcohol having 4 or less carbon atoms withat least one compound represented by the general formula ##STR4##(wherein R is an alkyl group, alkenyl group, alkylaryl preferablymonoalkylphenyl group, alkylarylalkyl preferably monoalkylbenzyl group,hydroxyalkyl group, acyl preferably alkyl- or alkenylcarbonyl group, orhydroxyl-substituted acyl preferably hydroxy-substituted alkyl- oralkenylcarbonyl group having 8 to 22 total carbon atoms, A is hydrogenatom or hydroxyl group, O≦W≦1, O≦X+Z≦3, O≦V≦3, 1≦a+b+c≦4) composed of aterminally monoalkylated polyalkylenepolyamine (the hydrocarbon radicalsinclude alkyl groups, alkenyl groups, alkylaryl preferablymonoalkylbenzyl groups, alkylarylalkyl preferably monoalkylbenzylgroups, hydroxyalkyl groups, alkoxyalkyl groups, alkoxyhydroxyalkylgroups, etc.), said polyalkylenepolyamine being obtained by the additionof 1 to 3 moles of ethyleneimine to 1 mole of ethylenediamine or1,3-propylenediamine or by the addition of acrylonitrile to said diaminefollowed by hydrogenation, said addition and hydrogenation beingrepeated 1 to 3 times (in each reaction cycle, 1 mole of acrylonitrileand 2 moles of hydrogen are used for 1 mole of the amine used asstarting material) or by carrying out the above both reactions; apolyalkylenepolyamine (the hydrocarbon groups thereof include alkylgroups, alkenyl groups, hydroxyalkyl groups, hydroxyalkenyl groups,etc.); and a monoalkylated (the hydrocarbon groups thereof include alkylgroups, alkenyl groups, alkylaryl preferably monoalkylphenyl groups,alkylarylalkyl preferably monoalkylbenzyl groups, hydroxyalkyl groups,alkoxyalkyl groups, alkoxyhydroxyalkyl groups, etc.) ethylenediamine and1,3-propylenediamine; or formed by reacting an acetoacetic ester orformylpropionic ester of an alcohol having 4 or less carbon atoms with1, 2, or more polyalkylenepolyamines obtained by the addition of 1 to 3moles of ethyleneimine to 1 mole of ethylenediamine or1,3-propylenediamine, or by 1 to 3 cycles of the addition ofacrylonitrile followed by hydrogenation (the molar ratio in eachreaction cycle is 1 mole of acrylonitrile and 2 moles of hydrogen for 1mole of the amine used as starting material), or by carrying out theabove both reactions, and then, further reacting with a carboxylic acidhaving an alkyl, alkenyl or hydroxyalkenyl group of 7 to 21 carbonatoms; or formed by reacting an acetoacetic ester or formylpropionicester of an alcohol having 4 or less carbon atoms with hydroxyethylatedethylenediamine, hydroxypropylated ethylenediamine, hydroxyethylated1,3-propylenediamine and hydroxypropylated 1,3-propylenediamine and thenfurther reacting with a carboxylic acid having an alkyl group, alkenylgroup, hydroxyalkyl group or hydroxyalkenyl group and/or reacting with amonochlorinated or monobrominated carboxylic acid or a salt thereof.

As for the polyalkylenepolyamines used as starting materials for theabove-said amines, mention may be made of ethylenediamine,diethylenetriamine, triethylenetetramine, tetraethylenepentamine, adductof 1,3-propylenediamine with 1 mole ethyleneimine, adduct of1,3-propylene diamine with 2 moles ethyleneimine, adduct of1,3-propylenediamine with 3 moles ethyleneimine, dipropylenetriamine,tripropylenetetramine, tetrapropylenepentamine, andpolyethylenepolypropylenepolyamine having 5 or less nitrogen atoms intotal. As for the monoalkylated products of these amines, there may becited monooctylated product, monononylated product, monodecylatedproduct, monoundecylated product, monododecylated product,monotridecylated product, monotetradecylated product, monopentadecylatedproduct, monohexadecylated product, monooctadecylated product,mono(9-octdecenyl)ated product, monoeicosylated product, monodocosylatedproduct, mono(2-hydroxy)dodecylated product,mono(2-hydroxy)hexadecylated product, mono(2-hydroxy)tetradecylatedproduct, mono(2-hydroxy)docosylated product,monooctoxy(2-hydroxy)propylated product,monononylphenoxy(2-hydroxy)propylated product,monododecoxy(2-hydroxy)propylated product, monooctylpoly(1-3moles)oxyethylated product, monononylpoly(1-3 moles)oxyethylatedproduct, monodecylpoly(1-3 moles)oxyethylated product,monoundecylpoly(1-3 moles)oxyethylated product, monododecylpoly(1-3moles)oxyethylated product, monotridecylpoly(1-3 moles)oxyethylatedproduct, monotetradecylpoly(1-3 moles)oxyethylated product,monopentadecylpoly(1-3 moles)oxyethylated product, monohexadecylpoly(1-3moles)oxyethylated product, monooctadecylpoly(1-3 moles)oxyethylatedproduct, mono(9-octadecenyl)poly(1-3 moles)oxyethylated product,monoeicosylpoly(1-3 moles)oxyethylated product, monodocosylpoly(1-3moles)oxyethylated product, monobutylphenylpoly(1-3 moles)oxyethylatedproduct, monooctylphenylpoly(1-3 moles)oxyethylated product,monononylphenylpoly(1-3 moles)oxyethylated product,monooctylpoly(1-3)oxypropylated product, monononylpoly(1-3moles)oxypropylated product, monodecylpoly(1-3 moles)oxypropylatedproduct, monododecylpoly(1-3 moles)oxypropylated product,monotridecylpoly(1-3 moles)oxypropylated product, monotetradecylpoly(1-3moles)oxypropylated product, monopentadecylpoly(1-3 moles)oxypropylatedproduct, monohexadecylpoly(1-3 moles)oxypropylated product,monooctadecylpoly(1-3 moles)oxypropylated product,mono(9-octadecenyl)poly(1-3 moles)oxypropylated product,monoeicosylpoly(1-3 moles)oxypropylated product, monodocosylpoly(1-3moles)oxypropylated product, monobutylphenyl(1-3 moles)oxypropylatedproduct, monooctylphenyl(1-3 moles)oxypropylated product,monononylphenyl(1-3 moles)oxypropylated product, monooctylpoly(2-3 molesin total)oxyethyloxypropylated product, monononylpoly(2-3 moles intotal)oxyethyloxypropylated product, monodecylpoly(2-3 moles intotal)oxyethyloxypropylated product, monoundecylpoly(2-3 moles intotal)oxyethyloxypropylated product, monododecylpoly(2-3 moles intotal)oxyethyloxypropylated product, monotridecylpoly(2-3 moles intotal)oxyethyloxypropylated product, monotetradecylpoly(2-3 moles intotal)oxyethyloxypropylated product, monopentadecylpoly(2-3 moles intotal)oxyethyloxypropylated product, monohexadecylpoly(2-3 moles intotal)oxyethyloxypropylated product, monooctadecylpoly(2-3 moles intotal)oxyethyloxypropylated product, mono(9-octadecenyl)poly(2-3 molesin total)oxyethyloxypropylated product, monoeicosylpoly(2-3 moles intotal)oxyethyloxypropylated product, monodocosylpoly(2-3moles)oxyethyloxypropylated product, monobutylphenylpoly(2-3 moles intotal)oxyethyloxypropylated product, monooctylphenylpoly(2-3 moles intotal)oxyethyloxypropylated product, and monononylphenylpoly(2-3 molesin total)oxyethyloxypropylated product. Amongmonohydroxyalkylalkylenediamines, there may be citedmonohydroxyethylethylenediamine, monohydroxyethyl1,3-propylenediamine,monohydroxypropylethylenediamine andmonohydroxypropyl-1,3-propylenediamine. As for the acetoacetic esters,on the other hand, mention may be made of methyl acetoacetate, ethylacetoacetate, propyl acetoacetate, isopropyl acetoacetate and butylacetoacetate. As for the formylpropionic esters, there may be citedmethyl, ethyl, propyl and butyl esters of 2-formylpropionic acid,3-formylpropionic acid, 2-formyl-2-methylpropionic acid and3-formyl-2-methylpropionic acid. Among carboxylic acids, mention may bemade of octylic acid, lauric acid, myristic acid, palmitic acid, stearicacid, oleic acid, linolic acid, 12-hydroxystearic acid, ricinolic acidand behenic acid. As for the monohalogenated carboxylic acids, there maybe cited monochloroacetic acid, monobromoacetic acid, andmonochloropropionic acid.

In producing the antibacterial surface active compound of thisinvention, the reaction between an acetoacetic ester or formylpropionicester and a monoamide prepared from a carboxylic acid and apolyalkylenepolyamine, N-alkylpolyalkylenepolyamine,N-alkoxyalkylpolyalkylenepolyamine, monohydroxyalkylalkylenediamine orpolyalkylenepolyamine is allowed to proceed by removing water or analcohol under reduced pressure or atmospheric pressure at 50° to 250°C., preferably 100° to 180° C., thus leading to theN-alkylazaalkenylactam of this invention. In this case, neither acatalyst nor a solvent is particularly needed, while bubbling of aninert gas such as nitrogen or carbon dioxide is effective inaccelerating the reaction. The reaction between anN-alkylazaalkenelactam and a monohalogenated carboxylic acid is allowedto proceed by bringing both into contact with each other at 30° to 100°C., preferably 50° to 80° C. in a polar solvent such as water, analcohol, dioxane or tetrahydrofuran in the presence of a water-solubleinorganic alkali such as sodium hydroxide or potassium hydroxide. On theother hand, the reaction between an N-alkylazaalkenelactam and a salt ofmonohalogenated carboxylic acid proceeds simply on being contacted witheach other at 30° to 100° C., preferably 50° to 80° C. in the presenceof the above-noted polar solvent, leading to the compound of thisinvention. Further, the reaction between a carboxylic acid and apolyalkylenepolyamine or a reaction product of a polyalkylenepolyamineand an acetoacetic ester or formylpropionic ester, and the reactionbetween a carboxylic acid and a reaction product of amonohydroxyalkylalkylenediamine and an acetoacetic ester orformylpropionic ester proceed, similarly to wellknown amide formationsand esterifications, by the dehydration under a reduced pressure oratmospheric pressure at 50° to 250° C., preferably 120° to 200° C. Inthese cases also neither a catalyst nor a reaction solvent isparticularly needed, while the bubbling of an inert gas such as nitrogenor carbon dioxide makes easier the completion of the reaction.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a diagrams of IR spectra of4-dodecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one (solid line) andits starting material ethyl acetoacetate (dotted line), respectively.(1) represents the absorption band of ν_(C)═O (ester), (2) that ofν_(C)═O (ketone), (3) that of ν_(C)═O (amide) and (4) that of ν_(C)═N.

FIG. 2 is the diagram of IR spectrum of4-dodecyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate which isthe final product in Example 1. (5) represents the absorption band of##STR5## and (6) represents that of ν_(C)═N⁺.

FIG. 3* and 4** are diagrams of 1H-NMR spectra of4-dodecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one and4-dodecyl-7-methyl-1-azonia-4-azacylohept-7-en-5-one-1-acetate,respectively.

FIG. 5 is the diagram of mass spectrum of4-dodecyl-7-methyl-3-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Further, since the N-alkylazaalkenelactams and their derivatives havingan organic acid radical, e.g. a carboxylate, which are the antibacterialsurface active compounds containing a cyclic amide according to thisinvention, exhibit, even in a small amount, antibacterial activityagainst aerobic bacteria, anaerobic bacteria, gram-positive bacteria andgram-negative bacteria, they act as bactericides on man, animals, andenvironment. Even more, they act as an inhibitor for the bacterialcorrosion of metals. Also, they themselves form a coating film onvarious metals to inhibit corrosion. Thus, these compounds are used asbactericides by themselves or, if necessary, in admixtures with variousdiluents.

BEST MODES FOR CARRYING OUT THE INVENTION

Examples are described below.

EXAMPLE 1

Into a four-necked flask provided with a stirrer, thermometer, gas inlettube, and water measuring tube connected with a reflux condenser, werecharged 228.1 g (1 mole) of N-dodecylethylenediamine and 130.1 g (1mole) of ethyl acetoacetate. While bubbling nitrogen gas, the flask washeated at 150° to 160° C. to distill off 18 g of water and 46 g ofethanol, and then 4-dodecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-onein slight yellow liquid was obtained.

Elementary analysis: C₁₈ H₃₄ ON₂ ; Calculated (%)--C 73.48, H 11.64, N9.52, Found (%)--C 73.50, H 11.65, N 9.55.

Amine value--192.0 (theoretical 190.8).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹. (ν_(C)═O, amide).

NMR spectrum-- ##STR6## proton 1.76 ppm (δ, TMS standard, 50 MHz).

Mass spectrum--(M+1) peak 295.

Subsequently, to a four-necked flask provided with a stirrer,thermometer, dropping funnel and an adapter for connecting with a refluxcondenser, were charged 116.5 g (1 mole) of sodium monochloroacetate and600 g of water to form a homogeneous solution. To the solution at 60° to70° C., was added dropwise 294.2 g (1 mole) of4-dodecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one to perform acetateradical formation at the same temperature and to synthesizewater-soluble4-dodecyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-on-1-acetate.

Elementary analysis: C₂₀ H₃₆ O₃ N₂ ; Calculated (%)--C 68.20, H 10.30, N7.95, Found (%)--C 68.18, H 10.32, N 7.96.

IR spectrum--1640 cm⁻¹ ##STR7##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.06 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 2

Into an apparatus similar to that in Example 1, were charged 271.1 g (1mole) of N-dodecyldiethylenetriamine and 116.1 g (1 mole) of methylacetoacetate. After 18 g of water and 32 g of methanol had beendistilled off at 140° to 150° C., there was obtained4-dodecylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one in slightred liquid.

Elementary analysis: C₂₀ H₃₉ ON₃ ; Calculated (%)--C 71.23, H 11.66, N12.45, Found (%)--C 71.26, H 11.69, N 12.44.

Amine value--333.1 (theoretical 332.8).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

NMR spectrum-- ##STR8## proton 1.78 ppm (δ, TMS standard, 50 MHz).

Mass spectrum (M+1) peak 338.

Subsequently, into a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 675 g of water, was added dropwise 337.2g (1 mole) of4-dodecylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one toperform acetate radical formation at 50° to 60° C. and to synthesize4-dodecylaminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₂ H₄₁ O₃ N₃ ; Calculated (%)--C 66.86, H 10.46, N10.63, Found (%)--C 66.83, H 10.45, N 10.67.

IR spectrum--1635 cm⁻¹ ##STR9##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 3

Into an apparatus similar to that in Example 1, were charged 242.1 g (1mole) of N-dodecyl-1,3-propylenediamine and 130.1 g (1 mole) of ethylacetoacetate. At 150° to 160° C., 18 g of water and 46 g of ethanol weredistilled off to obtain1-dodecyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₁₉ H₃₆ ON₂ ; Calculated (%)--C 74.04; H 11.77, N9.09, Found (%)--C 74.04, H 11.79, N 9.08.

Amine value--181.9 (theoretical 182.1)

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

NMR spectrum-- ##STR10## proton, 1.80 ppm (δ, TMS standard, 50 MHz).

Mass spectrum--(M+1) peak 309.

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 620 g of water, was added dropwise 308.2g (1 mole) of 1-dodecyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-oneto perform acetate radical formation as 60° to 70° C. and to synthesize1-dodecyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₁ H₃₈ O₃ N₂ ; Calculated (%)--C 68.67, H 10.46, N7.65, Found (%)--C 68.66, H 10.48, N 7.64.

IR spectrum--1635 cm⁻¹ ##STR11##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 4

Into an apparatus similar to that in Example 1, were charged 324.1 g (1mole) of N-(9-octadecenyl)-1,3-propylenediamine and 130.1 g (1 mole) ofethyl acetoacetate. At 110° to 120° C. and under a reduced pressure of50 mmHg, 18 g of water and 46 g of ethanol had been distilled off toobtain 1-(9-octadecenyl)-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₅ H₄₆ ON₂ ; Calculated (%)--C 76.95, H 11.88, N7.18, Found (%)--C 76.93, H 11.89, N 7.17.

Amine value--145.0 (theoretical 143.8)

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 700 g of water, was added dropwise 390.2g (1 mole) of1-(9-octadecenyl)-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one. Theacetate radical formation was effected at 70° to 80° C. to synthesize1-(9-octadecenyl)-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₇ H₄₈ O₃ N₂ ; Calculated (%)--C 72.35, H 10.80, N6.25, Found (%)--C 72.34, H 10.79, N 6.26.

IR spectrum--1635 cm⁻¹ ##STR12##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.07 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 5

Into an apparatus similar to that in Example 1, were charged 284.1 g (1mole) of N-hexadecylethylenediamine and 130.1 g (1 mole) of ethylacetoacetate. At 160° to 170° C., 18 g of water and 46 g of ethanol weredistilled off to obtain4-hexadecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₂ H₄₂ ON₂ ; Calculated (%)--C 75.45, H 12.09, N8.00, Found (%)--C 75.48, H 12.11, N 7.99.

Amine value--161.1 (theoretical 160.3).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, into a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 350.2g (1 mole) of 4-hexadecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-onedissolved in 350 g of dioxane. The acetate radical formation waseffected at 80° to 85° C. to synthesize4-hexadecyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₄ H₄₄ O₃ N₂ ; Calculated (%)--C 70.61, H 10.86, N6.86, Found (%)--C 70.64, H 10.86, N 6.88.

IR spectrum--1640 cm⁻¹ ##STR13##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 6

Into an apparatus similar to that in Example 1, were charged 315.1 g (1mole) of N-dodecoxyethyldiethylenetriamine and 130.1 g (1 mole) of ethylacetoacetate at 150° to 160° C., 18 g of water and 46 g of ethanol weredistilled off to obtain4-dodecoxyethylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₂ H₄₃ O₂ N₃ ; Calculated (%)--C 69.31, H 11.37, N11.02, Found (%)--C 69.29, H 11.39, N 10.98.

Amine value--296.1 (theoretical 294.4).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, into a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 700 g of water, was added dropwise 381.2g (1 mole) of4-dodecoxyethylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 60° to 70° C. tosynthesize4-dodecoxyaminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₄ H₄₅ O₄ N₃ ; Calculated (%)--C 65.63, H 10.33, N9.56, Found (%)--C 65.68, H 10.30, N 9.58.

IR spectrum--1640 cm⁻¹ ##STR14##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 7

Into an apparatus similar to that in Example 1, were charged 364.2 g (1mole) of N-nonylphenylpoly(2moles)oxyethyleneoxyethyl-1,3-propylenediamine and 130.1 g (1 mole) ofethyl acetoacetate. At 110° to 120° C. and under a reduced pressure of50 mmHg, 18 g of water and 46 g of ethanol were distilled off to obtain1-nonylphenylpoly(2moles)oxyethyleneoxyethyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₆ H₄₂ O₃ N₂ ; Calculated (%)--C 72.57, H 9.84, N6.51, Found (%)--C 72.55, H 9.87, N 6.48.

Amine value--128.2 (theoretical 130.4).

IR spectrum--1620 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, into a solution of 161.0 g (1 mole) of sodiummonobromoacetate dissolved in 500 g of water, was added dropwise 430.3 g(1 mole) of 1-nonylphenylpoly(2moles)oxyethyleneoxyethyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-onedissolved in 300 g of tetrahydrofuran. The acetate radical formation waseffected at 80° to 85° C. to synthesize 1-nonylphenylpoly(2moles)oxyethyleneoxyethyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₈ H₄₄ O₅ N₂ ; Calculated (%)--C 68.87, H 9.08, N5.73, Found (%)--C 68.85, H 9.09, N 5.77.

IR spectrum--1635 cm⁻¹ ##STR15##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 8

Into an apparatus similar to that in Example 1, were charged 230.1 g (1mole) of N-octoxypropylethylenediamine and 116.1 g (1 mole) of methylacetoacetate. At 140° to 145° C., 18 g of water and 32 g of ethanol weredistilled off to obtain4-octoxypropyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₁₇ H₃₂ O₂ N₂ ; Calculated (%)--C 68.93, H 10.89, N9.45, Found (%)--C 68.91, H 10.90, N 9.45.

Amine value--190.0 (theoretical 189.4).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 132.6 g (1 mole) of potassiummonochloroacetate dissolved in 600 g of water, was added dropwise 296.2g (1 mole) of 4-octoxypropyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 50° to 60° C. tosynthesize4-octoxypropyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₁₉ H₃₄ O₄ N₂ ; Calculated (%)--C 64.42, H 9.68, N7.91, Found (%)--C 64.46, H 9.66, N 7.89.

IR spectrum--1635 cm⁻¹ ##STR16##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.17 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 9

Into an apparatus similar to that in Example 1, were charged 103.1 g (1mole) of diethylenetriamine and 116.1 g (1 mole) of methyl acetoacetate.At 140° to 150° C., 18 g of water and 32 g of methanol were distilledoff. Then, with the addition of 200.3 g (1 mole) of lauric acid, theamide formation was effected at 200° to 210° C. and 18 g of water wasdistilled off, leaving behind4-lauramidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₀ H₃₇ O₂ N₃ ; Calculated (%)--C 68.37, H 10.62, N11.96, Found (%)--C 68.37, H 10.60, N 11.95.

Amine value--161.3 (theoretical 159.7).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 400 g of water, was added dropwise 351.3g (1 mole) of4-lauramidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one dissolved in350 g of methanol. The acetate radical formation was effected at 55° to60° C. to synthesize4-lauramidoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₂ H₃₉ O₄ N₃ ; Calculated (%)--C 64.55, H 9.60, N10.26, Found (%)--C 64.58, H 9.58, N 10.23.

IR spectrum--1640 cm⁻¹ ##STR17##

NMR spectrum N⁺ -CH₂ COO⁻ proton 2.03 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 10

Into an apparatus similar to that in Example 1, were charged 103.1 g (1mole) of diethylenetriamine and 116.1 g (1 mole) of methyl acetoacetate.At 110° to 120° C. and under a reduced pressure of 70 mmHg, 18 g ofwater and 32 g of methanol were distilled off. Then, with the additionof 282.5 g (1 mole) of oleic acid, the amide formation was effected at210° to 215° C. to distil off 18 g of water and to obtain4-oleamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₆ H₄₇ O₂ N₃ ; Calculated (%)--C 72.07, H 10.93, N9.69, Found (%)--C 72.04, H 10.97, N 9.66.

Amine value--131.0 (theoretical 129.6).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 161.0 g (1 mole) of sodiummonobromoacetate dissolved in 800 g of water, was added dropwise 433.3 g(1 mole) of 4-oleamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 70° to 80° C. tosynthesize4-oleamidoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₈ H₄₉ O₄ N₃ ; Calculated (%)--C 68.45, H 10.05, N8.55, Found (%)--C 68.44, H 10.01, N 8.58.

IR spectrum--1635 cm⁻¹ ##STR18##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.11 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 11

Into an apparatus similar to that in Example 1, were charged 103.1 g (1mole) of diethylenetriamine and 284.5 g (1 mole) of isostearic acid. At200° to 210° C., 18 g of water was distilled off to effect the monoamideformation. Then, after the addition of 130.1 g (1 mole) of ethylacetoacetate, 18 g of water and 46 g of ethanol were distilled off at150° to 160° C. to obtain4-isostearamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₆ H₄₉ O₂ N₃ ; Calculated (%)--C 71.73, H 11.35, N9.65, Found (%)--C 71.75, H 11.33, N 9.65.

Amine value--127.1 (theoretical 128.9).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g of sodium monochloroacetatedissolved in 800 g of water, was added dropwise 435.3 g (1 mole) of4-isostearamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. Theacetate radical formation was effected at 70° to 80° C. to synthesize4-isostearamidoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₈ H₅₁ O₄ N₃ ; Calculated (%)--C 68.17, H 10.42, N8.51, Found (%)--C 68.20, H 10.42, N 8.49.

IR spectrum--1630 cm⁻¹ ##STR19##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.05 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 12

Into an apparatus similar to that in Example 1, were charged 104.2 g (1mole) of N-hydroxyethylethylenediamine and 130.1 g (1 mole) of ethylacetoacetate. At 150° to 160° C., 18 g of water and 46 g of ethanol weredistilled off. Then, after addition of 200.3 g (1 mole) of lauric acid,the esterification was effected at 200° to 210° C. to distil off 18 g ofwater and to obtain4-lauroyloxyethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₀ H₃₆ O₃ N₂ ; Calculated (%)--C 68.12, H 10.29, N7.94, Found (%)--C 68.15, H 10.27, N 7.96.

Amine value--161.2 (theoretical 159.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide), 1740 cm⁻¹(ν_(C)═O, ester).

Subsequently, into a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 800 g of water, was added dropwise 352.6g (1 mole) of4-lauroyloxyethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. Theacetate radical formation was effected at 55° to 65° C. to synthesize4-lauroyloxyethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₂ H₃₈ O₅ N₂ ; Calculated (%)--C 64.35, H 9.33, N6.82, Found (%)--C 64.31, H 9.35, N 6.79.

IR spectrum--1635 cm⁻¹ ##STR20##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 13

Into an apparatus similar to that in Example 1, were charged 104.2 g (1mole) of N-hydroxyethylethylenediamine and 130.1 g (1 mole) ofethylacetoacetate. At 150° to 160° C., 18 g of water and 46 g of ethanolwere distilled off. Then, after addition of 282.5 g (1 mole) of oleicacid, the esterification was effected at 210° to 215° C. to distil off18 g of water and to obtain4-oleoyloxyethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₆ H₄₆ O₃ N₂ ; Calculated (%)--C 71.83, H 10.67, N6.44, Found (%)--C 71.85, H 10.69, N 6.44.

Amine value--130.6 (theoretical 129.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide) 1740 cm⁻¹(ν_(C)═O, ester).

Subsequently, to a solution of 434.7 g (1 mole) of4-oleoyloxyethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one dissolved in400 g of isopropyl alcohol, was added dropwise an aqueous solution of116.5 g (1 mole) of sodium monochloroacetate dissolved in 500 g ofwater. The acetate radical formation was effected at 60° to 70° C. tosynthesize4-oleoyloxyethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₈ H₄₈ O₅ N₂ ; Calculated (%)--C 68.25, H 9.82, N5.68, Found (%)--C 68.21, H 9.80, N 5.69.

IR spectrum--1630 cm⁻¹ ##STR21##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 14

Into an apparatus similar to that in Example 1, were charged 118.2 g (1mole) of N-hydroxyethyl-1,3-propylenediamine and 116.1 g (1 mole) ofmethyl acetoacetate. At 115° to 120° C. and under a reduced pressure of100 mmHg, 18 g of water and 32 g of methanol were distilled off. Then,after addition of 200.3 g (1 mole) of lauric acid, the esterificationwas effected at 190° to 200° C. to distil off 18 g of water and toobtain 1-lauroyloxyethyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₁ H₃₈ O₃ N₂ ; Calculated (%)--C 68.82, H 10.45, N7.64, Found (%)--C 68.79, H 10.47, N 7.66.

Amine value--153.0 (theoretical 153.1).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide), 1735 cm⁻¹(ν_(C)═O, ester).

Subsequently, to a solution of 177.0 g (1 mole) of potassiummonobromoacetate dissolved in 800 g of water, was added dropwise 366.5 g(1 mole) of1-lauroyloxyethyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one. Theacetate radical formation was effected at 55° to 65° C. to synthesize1-lauroyloxyethyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₃ H₄₀ O₅ N₂ ; Calculated (%)--C 65.07, H 9.50, N6.60, Found (%)--C 65.10, H 9.49, N 6.60.

IR spectrum--1635 cm⁻¹ ##STR22##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.07 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 15

Into an apparatus similar to that in Example 1, were charged 256.1 g (1mole) of N-coconutalkyl-1,3-propylenediamine (wherein, the carbon numbercomposition is 5% C₈, 10% C₁₀, 50% C₁₂, 20% C₁₄, 10% C₁₆ and 5% C₁₈) and116.1 g (1 mole) of methyl acetoacetate. At 145° to 155° C., 18 g ofwater and 32 g of methanol were distilled off to obtain1-coconutalkyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₀ H₃₈ ON₂ ; Calculated (%)--C 74.48, H 11.88, N8.68, Found (%)--C 74.51, H 11.90, N 8.65.

Amine value--175.1 (theoretical 174.0).

IR spectrum--1620 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 850 g of water, was added dropwise 322.5g (1 mole) of1-coconutalkyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one. Theacetate radical formation was effected at 70° to 80° C. to synthesize1-coconutalkyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₂ H₄₀ O₃ N₂ ; Calculated (%)--C 69.44, H 10.60, N7.36, Found (%)--C 69.40, H 10.59, N 7.39.

IR spectrum--1635 cm⁻¹ ##STR23##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 16

Into an apparatus similar to that in Example 1, were charged 301.5 g (1mole) of monooctylated 1,3-propylenediamine-poly(3 moles on theaverage)ethyleneimine adduct and 158.1 g (1 mole) of butyl acetoacetate.At 150° to 160° C. and under a reduced pressure of 50 mmHg, 18 g ofwater and 74 g of butanol were distilled off to synthesizeN-alkylalkenelactam.

Elementary analysis: C₂₁ H₄₂ ON₅ ; Calculated (%)--C 66.23, H 11.12, N18.38, Found (%)--C 66.23, H 11.10, N 18.41.

Amine value--592.1 (theoretical 589.4).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 94.5 g (1 mole) of monochloroacetic aciddissolved in 450 g of water, was added dropwise 380.8 g ofN-alkylalkenelactam obtained above. After mixing at 60° to 70° C. andfurther adding 40.0 g (1 mole) of sodium hydroxide, the reaction wasallowed to proceed at the same temperature to synthesize the compoundhaving anacetate radical.

Elementary analysis: C₂₃ H₄₄ O₃ N₅ ; Calculated (%)--C 62.95, H 10.11, N15.95, Found (%)--C 62.96, H 10.01, N 15.97.

IR spectrum--1640 cm⁻¹ ##STR24##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.03 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 17

Into an apparatus similar to that in Example 1, were charged 203.3 g (1mole) of 1,3-propylenediamine-poly(3 moles on the average)ethyleneimineadduct and 300.5 g (1 mole) of 12-hydroxystearic acid. At 220° to 225°C., 18 g of water was distilled off to effect the monoamide formation.Then, 116.1 g (1 mole) of methyl acetoacetate was charged. At 110° to115° C. and under a reduced pressure of 70 mm Hg, 18 g of water and 32 gof methanol were distilled off to synthesize N-alkylazaalkenelactam.

Elementary analysis: C₃₁ H₆₁ O₃ N₅ ; Calculated (%)--C 67.47, H 11.14, N12.69, Found (%)--C 67.46, H 11.12, N 12.71.

Amine value--306.1 (theoretical 305.0).

IR spectrum--1620 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).Subsequently, a solution of 139.0 g (1 mole) of monobromoacetic aciddissolved in 800 g of water and a solution of 551.8 g (1 mole) ofN-alkylazaalkenelactam dissolved in 500 g of tetrahydrofuran were mixedat 50° to 60° C. After addition of 40.0 g (1 mole) of sodium hydroxide,the reaction was allowed to proceed to form the compound having anacetate radical.

Elementary analysis: C₃₃ H₆₃ O₅ N₅ ; Calculated (%)--C 64.99, H 10.42, N11.48, Found (%)--C 64.96, H 10.42, N 11.45.

IR spectrum--1640 cm⁻¹ ##STR25##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.12 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 18

Into an apparatus similar to that in Example 1, were charged 528.8 g ofN-dodecylpoly(2 moles on theaverage)oxypropyleneoxypropylethylenediamine and 116.5 g (1 mole) ofmethyl acetoacetate. At 170° to 175° C., 18 g of water and 32 g ofmethanol were distilled off to synthesize N-alkylazaalkenelactam.

Elementary analysis: C₃₇ H₇₂ O₄ N₂ ; Calculated (%)--C 72.97, H 11.92, N4.60, Found (%)--C 73.00, H 11.88, N 4.62.

Amine value--92.0 (theoretical 92.1).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, a solution of 94.5 g (1 mole) of monochloroacetic acid in500 g of water and a solution of 609.0 g (1 mole) of theN-alkylazaalkenelactam in 600 g of dioxane were mixed at 70° to 80° C.After further addition of 56.1 g (1 mole) of potassium hydroxide, thereaction was allowed to proceed to form the compound having an acetateradical

Elementary analysis: C₃₉ H₇₄ O₆ N₂ ; Calculated (%)--C 70.22, H 11.18, N4.20, Found (%)--C 72.20, H 11.22, N 4.17.

IR spectrum--1640 cm⁻¹ ##STR26##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.07 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 19

Into an apparatus similar to that in Example 1, were charged 408.5 g (1mole) of N-octylphenoxyethyleneoxypropyleneoxypropylethylenediamine and116.5 g (1 mole) of methyl acetoacetate. At 170° to 175° C., 18 g ofwater and 32 g of methanol were distilled off to synthesizeN-alkylazaalkenelactam.

Elementary analysis: C₂₈ H₄₆ O₄ N₂ ; Calculated (%)--C 70.84, H 9.77, N5.90, Found (%) C 70.80, H 9.75, N 5.90.

Amine value--117.7 (theoretical 118.2).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).Subsequently, a solution of 94.5 g (1 mole) of monochloroacetic aciddissolved in 500 g of water and a solution of 474.7 g (1 mole) of theformed N-alkylazaalkenelactam dissolved in 500 g of isopropyl alcoholwere mixed at 65° to 75° C. After further addition of 40.0 g (1 mole) ofsodium hydroxide, the reaction was allowed to proceed to form thecompound having an acetate radical.

Elementary analysis: C₃₀ H₄₈ O₆ N₂ ; Calculated (%)--C 67.63, H 9.08, N5.26, Found (%)--C 67.60, H 9.08, N 5.23.

IR spectrum--1630 cm⁻¹ ##STR27##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 20

Into an apparatus similar to that in Example 1, were charged 429.6 g (1mole) of a monotridecoxyethyl derivative of 1,3-propylenediamine-poly(3moles on the average)ethyleneimine adduct and 130.1 g (1 mole) of ethylacetoacetate. At 165° to 170° C., 18 g of water and 46 g of ethanol weredistilled off to synthesize N-alkylazaalkenelactam.

Elementary analysis: C₂₈ H₅₇ O₂ N₅ ; Calculated (%)--C 67.83, H 11.59, N14.12, Found (%)--C 67.86, H 11.60, N 14.10.

Amine value--454.0 (theoretical 452.7).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 1,000 g of water, was added dropwise495.8 (1 mole) of the formed N-alkylazaalkenelactam. The reaction wasallowed to proceed at 60° to 70° C. to obtain the compound having anacetate radical.

Elementary analysis: C₃₀ H₅₉ O₄ N₅ ; Calculated (%)--C 65.07, H 10.74, N12.64, Found (%)--C 65.11, H 10.75, N 12.60.

IR spectrum--1635 cm⁻¹ ##STR28##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 21

Into an apparatus similar to that in Example 1, were charged 132.2 g (1mole) of N-hydroxypropyl-1,3-propylenediamine and 116.1 g (1 mole) ofmethyl acetoacetate. At 140° to 150° C., 18 g of water and 32 g ofmethanol were distilled off. After addition of 298.5 g (1 mole) ofricinolic acid, the esterification was effect at 220° to 225° C. todistil off 18 g of water and to synthesize N-alkylazaalkenelactam.

Elementary analysis: C₂₈ H₅₀ O₄ N₂ ; Calculated (%)--C 70.25, H 10.53, N5.85, Found (%)--C 70.30, H 10.55, N 5.86.

Amine value--117.1 (theoretical 117.2).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide), 1740 cm⁻¹(ν_(C)═O, ester).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 1,000 g of water, was added dropwise478.7 g (1 mole) of the formed N-alkylazaalkenelactam. The reaction wasallowed to proceed at 60° to 70° C. to obtain the compound having anacetate radical.

Elementary analysis: C₃₀ H₅₂ O₆ N₂ ; Calculated (%)--C 67.14, H 9.77, N5.22, Found (%)--C 67.12, H 9.76, N 5.23.

IR spectrum--1640 cm⁻¹ ##STR29##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 22

In a manner similar to that in Example 1, at first4-docosylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one wassynthesized using as starting materials 411.7 g (1 mole) ofN-docosyldiethylenetriamine and 130.1 g (1 mole) of ethyl acetoacetate.

Elementary analysis: C₃₀ H₅₉ ON₃ ; Calculated (%)--C 75.40, H 12.45, N8.79, Found (%)--C 75.38, H 12.46, N 8.82.

Amine value--234.0 (theoretical 234.9).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Then, 477.8 g (1 mole) of the formed4-docosylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one and 116.5g (1 mole) of sodium monochloroacetate were allowed to react in thepresence of 1,200 g of water to synthesize4-docosylaminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₃₂ H₆₁ O₃ N₃ ; Calculated (%)--C 71.73, H 11.48, N7.84, Found (%)--C 71.73, H 11.45, N 7.83.

IR spectrum--1635 cm⁻¹ ##STR30##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 23

In a manner similar to that in Example 9, using 103.1 g (1 mole) ofdiethylenetriamine 116.1 g (1 mole) of methyl acetoacetate, and 144.2 g(1 mole) of octylic acid as starting materials, at first4-octamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one wassynthesized.

Elementary analysis: C₁₆ H₂₉ O₂ N₃ ; Calculated (%)--C 65.09, H 9.90, N14.23, Found (%)--C 65.11, H 9.88, N 14.20.

Amine value--192.2 (theoretical 190.1).

IR spectrum--1620 cm⁻¹ (ν_(C)═O), 1660 cm⁻¹ (ν_(C)═O, amide).

Then, 295.2 g (1 mole) of the formed4-octamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one and 116.5 g(1 mole) of sodium monochloroacetate were allowed to react in thepresence of 600 g of water to synthesize4-octamidoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₁₈ H₃₁ O₄ N₃ ; Calculated (%)--C 61.21, H 8.85, N11.89, Found (%)--C 61.18, H 8.83, N 11.90.

IR spectrum--1635 cm⁻¹ ##STR31##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 24

In a manner similar to that in Example 12, using 104.2 g (1 mole) ofN-hydroxyethylethylenediamine, 130.1 g (1 mole) of ethyl acetoacetateand 144.2 g (1 mole) of octylic acid as starting materials, at first4-octoyloxyethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₁₆ H₂₈ O₃ N₂ ; Calculated (%)--C 64.83, H 9.52, N9.45, Found (%)--C 64.80, H 9.49, N 9.43.

Amine value--190.8 (theoretical 189.3).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide), 1740 cm⁻¹(ν_(C)═O, ester).

Then, 296.4 g (1 mole) of the formed4-octoyloxyethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one and 116.5 g(1 mole) of sodium monochloroacetate were allowed to react in thepresence of 750 g of water to synthesize4-octoyloxyethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₁₈ H₃₀ O₅ N₂ ; Calculated (%)--C 61.00, H 8.53, N7.90, Found (%)--C 60.95, H 8.50, N 7.93.

IR spectrum--1635 cm⁻¹ ##STR32##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 25

In a manner similar to that in Example 12, using 132.2 g (1 mole) ofN-hydroxypropyl-1,3-propylenediamine, 116.1 g (1 mole) of methylacetoacetate, and 340.5 g (1 mole) of behenic acid as startingmaterials, at first1-behenoyloxypropyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one wassynthesized.

Elementary analysis: C₃₂ H₅₈ O₃ N₂ ; Calculated (%)--C 74.08, H 11.27, N53.97, Found (%)--C 74.11, H 11.27, N 54.00.

Amine value--108.2 (theoretical 108.1).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide), 1735 cm⁻¹(ν_(C)═O, ester).

Then, 518.8 g (1 mole) of1-behenoyloxypropyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one and116.5 g (1 mole) of sodium monochloroacetate were allowed to react inthe presence of 600 g of water and 600 g of isopropyl alcohol tosynthesize1-behenoyloxypropyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₃₄ H₆₀ O₅ N₂ ; Calculated (%)--C 70.79, H 10.49, N4.85, Found (%)--C 70.81, H 10.51, N 4.84.

IR spectrum--1640 cm⁻¹ ##STR33##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.04 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 26

Into an apparatus similar to that in Example 1, were charged 244.8 g (1mole) of N-(2-hydroxy)dodecylethylenediamine and 116.1 g (1 mole) ofmethyl acetoacetate. At 140° to 150° C., 18 g of water and 32 g ofmethanol were distilled off to obtain white wax-like4-(2-hydroxy)dodecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₁₈ H₃₄ O₂ N₂ ; Calculated (%)--C 69.56, H 11.03, N9.01, Found (%)--C 69.39, H 11.06, N 9.07.

Amine value--180.6 (theoretical 180.5).

IR spectrum--1620 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added a solution of310.8 g (1 mole) of4-(2-hydroxy)dodecyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-onedissolved in 150 g of dioxane. The acetate radical formation waseffected at 50° to 60° C. to obtain4-(2-hydroxy)dodecyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₀ H₃₆ O₄ N₂ ; Calculated (%)--C 65.13, H 9.84, N7.59, Found (%)--C 65.17, H 9.80, N 7.57.

IR spectrum--1635 cm⁻¹ ##STR34##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 27

Into an apparatus similar to that in Example 1, were charged 284.5 g (1mole) of N-(2-hydroxy)tetradecylpropylenediamine and 130.1 g (1 mole) ofethyl acetoacetate. At 150° to 160° C., 18 g of water and 46 g ofethanol were distilled off to obtain white waxy1-(2-hydroxy)tetradecyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₁ H₃₈ O₂ N₂ ; Calculated (%)--C 71.96, H 10.93, N7.99, Found (%)--C 71.96, H 10.97, N 8.03.

Amine value--160.3 (theoretical 160.1).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added a solution of350.5 g (1 mole) of1-(2-hydroxy)tetradecyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-onedissolved in 200 g of ethanol. The acetate radical formation waseffected at 50° to 60° C. to obtain1-(2-hydroxy)tetradecyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₃ H₄₀ O₄ N₂ ; Calculated (%)--C 67.62, H 9.87, N6.85, Found (%)--C 67.60, H 9.91, N 6.89.

IR spectrum--1640 cm⁻¹ ##STR35##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.11 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 28

Into an apparatus similar to that in Example 1, were charged 313.5 g (1mole) of N-(2-hydroxy)tetradecyldiethylenetriamine and 158.1 g (1 mole)of butyl acetoacetate. At 150° to 160° C. and under a reduced pressureof 50 mmHg, 18 g of water and 74 g of butanol were distilled off toobtain4-(2-hydroxytetradecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₂ H₄₁ O₂ N₃ ; Calculated (%)--C 69.62, H 10.89, N11.07, Found (%)--C 69.65, H 10.85, N 11.10.

Amine value--296.0 (theoretical 295.7).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 94.5 g (1 mole) of monochloroacetic aciddissolved in 450 g of water, was added dropwise 379.5 g (1 mole) of theformed4-(2-hydroxytetradecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.After mixing at 60° to 70° C. and further addition of 40.0 g (1 mole) ofsodium hydroxide, the reaction was allowed to proceed at the sametemperature to obtain4-(2-hydroxytetradecyl)aminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₄ H₄₃ O₄ N₃ ; Calculated (%)--C 65.88, H 9.91, N9.60, Found (%)--C 65.86, H 9.90, N 9.58.

IR spectrum--1645 cm⁻¹ ##STR36##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 29

Into an apparatus similar to that in Example 1, were charged 339.5 g (1mole) of N-(2-hydroxy)hexadecyldiethylenetriamine and 116.1 g (1 mole)of methyl acetoacetate. At 140° to 150° C., 18 g of water and 32 g ofmethanol were distilled off to obtain4-(2-hydroxyhexadecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₄ H₄₃ O₂ N₃ ; Calculated (%)--C 71.08, H 10.69, N10.36, Found (%)--C 71.03, H 10.70, N 10.36.

Amine value--276.2 (theoretical 276.7).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 405.5 g (1 mole) of4-(2-hydroxyhexadecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-onedissolved in 200 g of isopropyl alcohol, was added 132.6 g (1 mole) ofpotassium monochloroacetate dissolved in 600 g of water. The acetateradical formation was effected at 60° to 70° C. to obtain4-(2-hydroxyhexadecyl)aminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₆ H₄₅ O₄ N₃ ; Calculated (%)--C 67.37, H 9.79, N9.06, Found (%)--C 67.40, H 9.82, N 9.07.

IR spectrum--1645 cm⁻¹ ##STR37##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 30

Into an apparatus similar to that in Example 1, were charged 484.8 g (1mole) of a mono(2-hydroxy)docosyl derivative of a1,3-propylenediamine-poly-(2 moles on the average)ethyleneimine adductand 116.1 g (1 mole) of methyl acetoacetate. At 160° to 170° C., 18 g ofwater and 32 g of methanol were distilled off to obtain1-(2-hydroxy)aminoethylaminoethyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₃₃ H₆₆ O₂ N₄ ; Calculated (%)--C 71.96, H 12.08, N10.17, Found (%)--C 71.80, H 12.06, N 10.18.

Amine value--308.8 (theoretical 305.6).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 161.0 g (1 mole) of sodiummonochloroacetate dissolved in 900 g of water, was added dropwise 550.8g (1 mole) of1-(2-hydroxy)docosylaminoethylaminoethyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.The acetate radical formation was effected at 70° to 80° C. to obtain1-(2-hydroxy)docosylaminoethylaminoethyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₃₅ H₆₈ O₄ N₄ ; Calculated (%)--C 69.04, H 11.26, N9.20, Found (%)--C 69.00 H 11.30, N 9.19.

IR spectrum--1640 cm⁻¹ ##STR38##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.13 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 31

Into an apparatus similar to that in Example 1, were charged 218.3 g (1mole) of N-octoxy(2-hydroxy)propylethylenediamine and 130.1 g (1 mole)of ethyl acetoacetate. At 150° to 160° C., 18 g of water and 46 g ofethanol were distilled off to obtain4-octoxy(2-hydroxy)propyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₁₅ H₂₈ O₃ N₂ ; Calculated (%)--C 63.36, H 9.93, N9.85, Found (%)--C 63.35, H 9.92, N 9.88.

Amine value--197.3 (theoretical 197.3).

IR spectrum--1620 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 284.3g (1 mole) of4-octoxy(2-hydroxy)propyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 50° to 60° C. to obtain4-octoxy(2-hydroxy)propyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₁₇ H₃₀ O₅ N₂ ; Calculated (%)--C 59.64, H 8.83, N8.18, Found (%)--C 59.60, H 8.83, N 8.21.

IR spectrum--1650 cm⁻¹ ##STR39##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.11 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 32

Into an apparatus similar to that in Example 1, were charged 465.7 g (1mole) of N-nonylphenoxy(2-hydroxy)propyltetraethylenepentamine and 130.1g (1 mole) of ethyl acetoacetate. At 150° to 160° C., 18 g of water and46 g of ethanol were distilled off to obtain4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₃₀ H₅₃ O₃ N₅ ; Calculated (%)--C 67.77, H 10.05, N13.17, Found (%)--C 67.80, H 10.06, N 13.16.

Amine value--424.0 (theoretical 422.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 177.0 g (1 mole) of potassiummonobromoacetate dissolved in 1,000 g of water, was added 531.7 g (1mole) of4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 50° to 55° C. to obtain4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₃₂ H₅₅ O₅ N₅ ; Calculated (%)--C 65.18, H 9.40, N11.87, Found (%)--C 65.15, H 9.41, N 11.90.

IR spectrum--1655 cm⁻¹ ##STR40##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.11 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 33

Into an apparatus similar to that in Example 1, were charged 316.5 g (1mole) of N-docoxy(2-hydroxy)propylpropylenediamine and 116.1 g (1 mole)of methyl acetoacetate. At 145° to 155° C., 18 g of water and 32 g ofmethanol were distilled off to obtain1-docoxy(2-hydroxy)propyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₂ H₄₂ O₃ N₂ ; Calculated (%)--C 69.08, H 11.07, N7.32, Found (%)--C 69.08, H 11.09, N 7.35.

Amine value--146.7 (theoretical 146.7).

IR spectrum--1617 cm⁻¹ (ν_(C)═O), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 107.6 g (1 mole) of monochloropropionicacid dissolved in 450 g of water, was added dropwise 382.5 g (1 mole) of1-docoxy(2-hydroxy)propyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.After mixing at 50° to 60° C. and adding a solution of 56.1 g (1 mole)of potassium hydroxide dissolved in 200 g of water, the reaction wasallowed to proceed at the same temperature to obtain1-docoxy(2-hydroxy)propyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-propionate.

Elementary analysis: C₂₅ H₄₆ O₅ N₂ ; Calculated (%)--C 66.06, H 10.20, N6.16, Found (%)--C 66.10, H 10.18, N 6.18.

IR spectrum--1645 cm⁻¹ ##STR41##

NMR spectrum-- ##STR42## methyne proton 2.40 ppm (δ, DSS standard, 50MHz).

EXAMPLE 34

Into an apparatus similar to that in Example 1, were charged 314.5 g (1mole) of N-dodecyltriethylenetetramine and 116.1 g (1 mole) of methylacetoacetate. At 140° to 150° C., 18 g of water and 32 g of methanolwere distilled off to obtain4-dodecylaminoethylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₂ H₄₄ ON₄ ; Calculated (%)--C 69.42, H 11.65, N14.71, Found (%)--C 69.48, H 11.68, N 14.72.

Amine value--444.2 (theoretical 442.2).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 700 g of water, was added dropwise 380.6g (1 mole) of4-dodecylaminoethylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 50° to 60° C. tosynthesize4-dodecylaminoethylaminoethyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₄ H₄₆ O₃ N₄ ; Calculated (%)--C 65.72, H 10.57, N12.77, Found (%)--C 65.75, H 10.55, N 12.79.

IR spectrum--1640 cm⁻¹ ##STR43##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHZ).

EXAMPLE 35

Into an apparatus similar to that in Example 1, were charged 299.5 g (1mole) of N-tetradecyldiethylenetriamine and 116.1 g (1 mole) of methylacetoacetate. At 150° to 160° C., 18 g of water and 32 g of methanolwere distilled off to obtain4-tetradecylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₂ H₄₃ ON₃ ; Calculated (%)--C 72.27, H 11.86, N11.49, Found (%)--C 72.26, H 11.88, N 11.52.

Amine value--306.8 (theoretical 306.9).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 700 g of water, was added dropwise 365.6g (1 mole) of4-tetradecylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. Theacetate radical formation was effected at 60° to 70° C. to obtain4-tetradecylaminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₄ H₄₅ O₃ N₃ ; Calculated (%)--C 68.05, H 10.71, N9.92; Found (%)--C 68.06, H 10.73, N 9.91.

IR spectrum--1635 cm⁻¹ ##STR44##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 36

Into an apparatus similar to that in Example 1, were charged 299.5 g (1mole) of N-dodecyldipropylenetriamine and 130.1 g (1 mole) of ethylacetoacetate. At 150° to 160° C., 18 g of water and 46 g of ethanol weredistilled off to obtain1-dodecylaminopropyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₂ H₄₃ ON₃ ; Calculated (%)--C 72.29, H 11.86, N11.49, Found (%)--C 72.33, H 11.88, N 11.46.

Amine value--308.1 (theoretical 307.0).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 132.6 g (1 mole) of potassiummonochloroacetate dissolved in 800 g of water, was added dropwise 365.5g (1 mole) of1-dodecylaminopropyl-4methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one. Theacetate radical formation was effected at 60° to 70° C. to obtain1-dodecylaminopropyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₄ H₄₅ O₃ N₃ ; Calculated (%)--C 68.06, H 10.71, N9.92, Found (%)--C 68.09, H 10.72, N 9.95.

IR spectrum--1635 cm⁻¹ ##STR45##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.06 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 37

Into an apparatus similar to that in Example 1, were charged 381.7 g (1mole) of N-octadecyldipropylenetriamine and 130.1 g (1 mole) of ethylacetoacetate. At 150° to 160° C., 18 g of water and 46 g of ethanol weredistilled off to obtain1-octadecylaminopropyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₈ H₅₃ ON₃ ; Calculated (%)--C 75.11, H 11.93, N9.38, Found (%)--C 75.14, H 11.93, N 9.40.

Amine value--250.9 (theoretical 250.6).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 107.6 g (1 mole) of monochloropropionicacid dissolved in 600 g of water, was added dropwise 447.7 g (1 mole) of1-octadecylaminopropyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.After mixing at 70° to 80° C. and adding 40.0 g (1 mole) of sodiumhydroxide, the reaction was allowed to proceed at the same temperatureto obtain1-octadecylaminopropyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-propionate.

Elementary analysis: C₃₁ H₅₇ O₃ N₃ ; Calculated (%)--C 71.63, H 11.05, N8.08, Found (%)--C 71.60, H 11.08, N 8.09.

IR spectrum--1640 cm⁻¹ ##STR46##

NMR spectrum-- ##STR47## methyne proton 2.36 ppm (δ, DSS standard, 50MHz).

EXAMPLE 38

Into an apparatus similar to that in Example 1, were charged 385.6 g (1mole) of a monododecyl-derivative of an adduct of dipropylenetriaminewith 2 moles of ethyleneimine and 158.1 g of butyl acetoacetate. At 155°to 160° C. and under a reduced pressure of 40 mmHg, 18 g of water and 74g of butanol were distilled off to obtain1-dodecylaminoethylaminoethylaminopropyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₆ H₅₃ ON₅ ; Calculated (%)--C 69.15, H 11.83, N15.50, Found (%)--C 69.20, H 11.87, N 15.53.

Amine value--500.0 (theoretical 496.9).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C=) O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 800 g of water, was added dropwise 451.6g (1 mole) of1-dodecylaminoethylaminoethylaminopropyl-4-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.The acetate radical formation was effected at 60° to 70° C. to obtain1-dodecylaminoethylaminoethylaminopropyl-4-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₈ H₅₅ O₃ N₅ ; Calculated (%)--C 65.99, H 10.88, N13.74, Found (%)--C 66.03, H 10.85, N 13.80.

IR spectrum--1640 cm⁻¹ ##STR48##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 39

Into an apparatus similar to that in Example 1, were charged 338.5 g (1mole) of N-methylbenzylpoly(2 moles)oxypropyleneoxypropylethylenediamineand 116.1 g (1 mole) of methyl acetoacetate. At 140° to 150° C., 18 g ofwater and 32 g of methanol were distilled off to obtain4-methylbenzylpoly(2moles)oxypropyleneoxypropyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₃ H₃₆ O₄ N₂ ; Calculated (%)--C 68.29, H 8.97, N6.92, Found (%)--C 68.32, H 8.95, N 6.93.

Amine value--139.5 (theoretical 138.7).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodium chloroacetatedissolved in 600 g of water, was added dropwise 404.5 g (1 mole) of4-methylbenzylpoly(2moles)oxypropyleneoxypropyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 50° to 60° C. to obtain4-methylbenzylpoly(2moles)oxypropyleneoxypropyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₅ H₃₈ O₆ N₂ ; Calculated (%)--C 64.92, H 8.28, N6.05, Found (%)--C 64.96, H 8.26, N 6.06.

IR spectrum--1640 cm⁻¹ ##STR49##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 40

Into an apparatus similar to that in Example 1, were charged 299.5 g (1mole) of N-tetradecyldiethylenetriamine and 116.1 g (1 mole) of methyl2-formylpropionate. At 130° to 135° C., 18 g of water and 32 g ofmethanol were distilled off to obtain4-tetradecylaminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₂ H₄₃ ON₃ ; Calculated (%)--C 72.27, H 11.86, N11.49, Found (%)--C 72.30, H 11.88, N 11.46.

Amine value--306.8 (theoretical 306.9).

IR spectrum--1618 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 365.6g (1 mole) of4-tetradecylaminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. Theacetate radical formation was effected at 50° to 60° C. to obtain4-tetradecylaminoethyl-6-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₄ H₄₅ O₃ N₃ ; Calculated (%)--C 68.05, H 10.71, N9.92, Found (%)--C 68.03, H 10.73, N 9.94.

IR spectrum--1635 cm⁻¹ ##STR50##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 41

Into an apparatus similar to that in Example 1, were charged 339.5 g (1mole) of N-(2-hydroxy)hexadecyldiethylenetriamine and 130.1 g of ethyl2-formylpropionate. At 140° to 150° C., 18 g of water and 46 g ofethanol were distilled off to obtain4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₄ H₄₃ O₂ N₃ ; Calculated (%)--C 71.08, H 10.69, N10.36, Found (%)--C 71.10, H 10.71, N 10.36.

Amine value--276.5 (theoretical 276.7).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 405.5 g (1 mole) of4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-onedissolved in 200 g of dioxane, was added a solution of 132.6 g (1 mole)of potassium monochloroacetate dissolved in 600 g of water. The acetateradical formation was effected at 60° to 70° C. to obtain4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₆ H₄₅ O₄ N₃ ; Calculated (%)--C 67.37, H 9.79, N9.06, Found (%)--C 67.41, H 9.78, N 9.06.

IR spectrum--1645 cm⁻¹ ##STR51##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 42

Into an apparatus similar to that in Example 1, were charged 228.1 g (1mole) of N-dodecylethylenediamine and 130.1 g (1 mole) of ethyl2-formylpropionate. At 140° to 145° C., 18 g of water and 46 g ofethanol were distilled off to obtain4-dodecyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₁₈ H₃₄ ON₂ ; Calculated (%)--C 73.48, H 11.64, N9.52, Found (%)--C 73.51, H 11.68, N 9.54.

Amine value--192.1 (theoretical 190.8).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 294.2g (1 mole) of 4-dodecyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. Theacetate radical formation was effected at 50° to 60° C. to obtain4-dodecyl-6-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₀ H₃₆ O₃ N₂ ; Calculated (%)--C 68.20, H 10.30, N7.95, Found (%)--C 68.25, H 10.31, N 7.98.

IR spectrum--1640 cm⁻¹ ##STR52##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.05 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 43

Into an apparatus similar to that in Example 1, were charged 244.8 g (1mole) of N-(2-hydroxy)dodecylethylenediamine and 144.2 g (1 mole) ofisopropyl 2-formylpropionate. At 150° to 155° C., 18 g of water and 60 gof isopropyl alcohol were distilled off to obtain4-(2-hydroxy)dodecyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₁₈ H₃₄ O₂ N₂ ; Calculated (%)--C 69.56, H 11.03, N9.01, Found (%)--C 69.39, H 11.05, N 9.05.

Amine value--180.5 (theoretical 180.5).

IR spectrum--1620 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added a solution of310.8 g (1 mole) of4-(2-hydroxy)dodecyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-onedissolved in 150 g of ethanol. The acetate radical formation waseffected at 50° to 60° C. to obtain4-(2-hydroxy)dodecyl-6-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₀ H₃₆ O₄ N₂ ; Calculated (%)--C 65.13, H 9.84, N7.59, Found (%)--C 65.15, H 9.80, N 7.60.

IR spectrum--1635 cm⁻¹ ##STR53##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 44

Into an apparatus similar to that in Example 1, were charged 242.1 g (1mole) of N-dodecylpropylenediamine and 130.1 g (1 mole) of ethyl2-formylpropionate. At 145° to 150° C., 18 g of water and 46 g ofethanol were distilled off to obtain1-dodecyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₁₉ H₃₆ ON₂ ; Calculated (%)--C 74.04, H 11.77, N9.09, Found (%)--C 74.03, H 11.76, N 9.09.

Amine value--181.9 (theoretical 182.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 308.2g (1 mole) of 1-dodecyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.The acetate radical formation was effected at 60° to 70° C. to obtain1-dodecyl-3-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₁ H₃₈ O₃ N₂ ; Calculated (%)--C 68.67, H 10.46, N7.65, Found (%)--C 68.68, H 10.49, N 7.65.

IR spectrum--1635 cm⁻¹ ##STR54##

NMR spectrum--N⁺ -CH₂ -COO⁻ proton 2.09 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 45

Into an apparatus similar to that in Example 1, were charged 256.5 g (1mole) of N-(2-hydroxy)dodecylpropylenediamine and 116.1 g (1 mole) ofmethyl 2-formylpropionate. At 130° to 135° C., 18 g of water and 32 g ofmethanol were distilled off to obtain1-(2-hydroxy)dodecyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₁₉ H₃₄ O₂ N₂ ; Calculated (%)--C 75.97, H 10.63, N8.68, Found (%)--C 76.00, H 10.62, N 8.71.

Amine value--174.1 (theoretical 173.9).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, into a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 322.5g (1 mole) of1-(2-hydroxy)dodecyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one. Theacetate radical formation was effected at 50° to 60° C. to obtain1-(2-hydroxy)dodecyl-3-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₁ H₃₆ O₄ N₂ ; Calculated (%)--C 66.28, H 9.54, N7.36, Found (%)--C 66.30, H 9.50, N 7.38.

IR spectrum--1635 cm⁻¹ ##STR55##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 46

Into an apparatus similar to that in Example 1, were charged 103.1 g (1mole) of diethylenetriamine and 116.1 g (1 mole) of methyl2-formylpropionate. At 130° to 135° C., 18 g of water and 32 g ofmethanol were distilled off. Then, after addition of 200.3 g (1 mole) oflauric acid, the amide formation was effected at 200° to 210° C. todistil off 18 g of water, leaving behind4-lauramidoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₀ H₃₇ O₂ N₃ ; Calculated (%)--C 68.37, H 10.62, N11.96, Found (%)--C 68.38, H 10.62, N 11.99.

Amine value--161.2 (theoretical 159.7).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 400 g of water, was added dropwise asolution of 351.3 g (1 mole) of4-lauramidoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one dissolved in400 g of methanol. The acetate radical formation was effected at 55° to60° C. to obtain4-lauramidoethyl-6-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₂ H₃₉ O₄ N₃ ; Calculated (%)--C 64.55, H 9.60, N10.26, Found (%)--C 64.58, H 9.61, N 10.23.

IR spectrum--1640 cm⁻¹ ##STR56##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.06 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 47

Into an apparatus similar to that in Example 1, were charged 104.2 g (1mole) of N-hydroxyethylenediamine and 130.1 g (1 mole) of ethyl2-formylpropionate. At 145° to 150° C., 18 g of water and 46 g ofethanol were distilled off. Then, after addition of 200.3 g (1 mole) oflauric acid, esterification was carried out while distilling off 18 g ofwater to obtain4-lauroyloxyethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₀ H₃₆ O₃ N₂ ; Calculated (%)--C 68.12, H 10.29, N7.94, Found (%)--C 68.15, H 10.28, N 7.96.

Amine value--159.5 (theoretical 159.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide), 1740 cm⁻¹(ν_(C)═O, ester).

Subsequently, to 116.5 g (1 mole) of sodium monochloroacetate dissolvedin 800 g of water, was added dropwise 352.6 g (1 mole) of4-lauroyloxyethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. Theacetate radical formation was carried out at 60° to 70° C. toobtain.4-lauroyloxyethyl-6-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₂ H₃₈ O₅ N₂ ; Calculated (%)--C 64.35, H 9.33, N6.82, Found (%)--C 64.36, H 9.36, N 6.78.

IR spectrum--1635 cm⁻¹ ##STR57##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 48

Into an apparatus similar to that in Example 1, were charged 313.5 g (1mole) of N-monotetradecylaminoethylpropylenediamine and 116.1 g (1 mole)of methyl-2-formylpropionate. At 130° to 135° C., 18 g of water and 32 gof methanol were distilled off to obtain1-tetradecylaminoethyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₃ H₄₅ ON₃ ; Calculated (%)--C 72.76, H 11.96, N11.06, Found (%)--C 72.77, H 11.99, N 11.08.

Amine value--295.4 (theoretical 295.6).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 107.6 g (1 mole) of monochloropropionicacid dissolved in 600 g of water, was added dropwise 379.6 g (1 mole) of1-tetradecylaminoethyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.After mixing at 70° to 80° C. and addition of 40.0 g (1 mole) of sodiumhydroxide, the reaction was allowed to proceed at the same temperatureto obtain 1-tetradecylaminoethyl-3-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-propionate.

Elementary analysis: C₂₆ H₄₉ O₃ N₃ ; Calculated (%)--C 69.14, H 10.94, N9.30, Found (%)--C 69.15, H 10.95, N 9.32.

IR spectrum--1645 cm⁻¹ ##STR58##

NMR spectrum-- ##STR59## methyne proton 2.40 ppm (δ, DSS standard, 50MHz).

EXAMPLE 49

Into an apparatus similar to that in Example 1, were charged 353.5 g (1mole) of N-mono(2-hydroxy)hexadecylaminoethylpropylenediamine and 158.2g (1 mole) of butyl 2-formyl propionate. At 155° C. and under a reducedpressure of 50 mmHg, 18 g of water and 74 g of butanol were distilledoff to obtain1-(2-hydroxyhexadecyl)aminoethyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₂₅ H₄₅ O₂ N₃ ; Calculated (%)--C 71.55, H 10.82, N10.01, Found (%)--C 71.59, H 10.81, N 10.00.

Amine value--268.0 (theoretical 267.3)

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 419.7 g (1 mole) of1-(2-hydroxyhexadecyl)aminoethyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-onedissolved in 250 g of isopropyl alcohol, was added a solution of 132.6 g(1 mole) of potassium monochloroacetate dissolved in 600 g of water. Theacetate radical formation was effected at 60° to 70° C. to obtain1-(2-hydroxyhexadecyl)aminoethyl-3-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₇ H₄₇ O₄ N₃ ; Calculated (%)--C 67.89, H 9.92, N8.79, Found (%)--C 67.92, H 9.89, N 8.81.

IR spectrum--1645 cm⁻¹ ##STR60##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 50

Into an apparatus similar to that in Example 1, were charged 301.5 g (1mole) of a monooctyl derivative of a 1,3-propylenediamine-poly(3moles onthe average)ethyleneimine adduct and 130.1 g (1 mole) of ethyl2-formylpropionate. At 130° to 140° C. and under a reduced pressure of50 mmHg, 18 g of water and 46 g of ethanol were distilled off tosynthesize N-alkylalkenelactam.

Elementary analysis: C₂₁ H₄₂ ON₅ ; Calculated (%)--C 66.23, H 11.12, N18.38, Found (%)--C 66.28, H 11.14, N 18.33.

Amine value--590.1 (theoretical 589.4).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 94.5 g (1 mole) of monochloroacetic aciddissolved in 500 g of water, was added dropwise 380.8 g (1 mole) of theformed N-alkylalkenelactam. After mixing at 60° to 70° C. and additionof 56.1 g (1 mole) of potassium hydroxide, the reaction was allowed toproceed at the same temperature to obtain the compound having an acetateradical.

Elementary analysis: C₂₃ H₄₄ O₃ N₅ ; Calculated (%)--C 62.95, H 10.11, N15.95, Found (%)--C 62.99, H 10.98, N 15.95.

IR spectrum--1640 cm⁻¹ ##STR61##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.05 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 51

Into an apparatus similar to that in Example 1, were charged 132.2 g (1mole) of N-hydroxypropyl-1,3-propylenediamine and 116.1 g (1 mole) ofmethyl 2-formylpropionate. At 130° to 135° C., 18 g of water and 32 g ofmethanol were distilled off. Then, after adding 340.5 g (1 mole) ofbehenic acid, esterification was carried out at 180° to 190° C. under areduced pressure of 70 mmHg, while distilling off 18 g of water, toobtain1-behenoyloxypropyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.

Elementary analysis: C₃₂ H₅₈ O₃ N₂ ; Calculated (%)--C 74.08, H 11.27, N53.98, Found (%)--C 74.10, H 11.27, N 53.98.

Amine value--108.3 (theoretical 108.1).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide), 1735 cm⁻¹(ν_(C)═O, ester).

Subsequently, to a solution of 518.8 g (1 mole) of1-behenoyloxypropyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-onedissolved in 600 g of isopropyl alcohol, was added dropwise a solutionof 177.0 g (1 mole) of potassium monobromoacetate dissolved in 600 g ofwater. The acetate radical formation was effected at 70° to 80° C. toobtain1-behenoyloxypropyl-3-methyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₃₄ H₆₀ O₅ N₂ ; Calculated (%)--C 70.79, H 10.49, N4.85, Found (%)--C 70.82, H 10.51, N 4.85.

IR spectrum--1640 cm⁻¹ ##STR62##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.05 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 52

Into an apparatus similar to that in Example 1, were charged 465.7 g (1mole) of N-nonylphenoxy(2-hydroxy)propyltetraethylenepentamine and 130.1g (1 mole) of ethyl 2-formylpropionate. At 140° to 145° C., 18 g ofwater and 46 g of ethanol were distilled off to obtain4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₃₀ H₅₃ O₃ N₅ ; Calculated (%)--C 67.77, H 10.05, N13.17, Found (%)--C 67.81, H 10.05, N 13.19.

Amine value--423.5 (theoretical 422.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═O), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 177.0 g (1 mole) of potassiummonobromoacetate dissolved in 1,000 g of water, was added 531.7 g (1mole) of4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 60° to 70° C. to obtain4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-6-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₃₂ H₅₅ O₅ N₅ ; Calculated (%)--C 65.18, H 9.40, N11.87, Found (%)--C 65.18, H 9.39, N 11.88.

IR spectrum--1650 cm⁻¹ ##STR63##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 53

Into an apparatus similar to that in Example 1, were charged 299.5 g (1mole) of N-tetradodecyldiethylenetriamine and 116.1 g (1 mole) of methyl3-formylpropionate. At 125° to 130° C., 18 g of water and 32 g ofmethanol were distilled off to obtain4-tetradecylaminoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₂₂ H₄₃ ON₃ ; Calculated (%)--C 72.27, H 11.86, N11.49, Found (%)--C 72.31, H 11.87, N 11.48.

Amine value--306.8 (theoretical 306.9)

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 700 g of water, was added dropwise 365.6g (1 mole) of4-tetradecylaminoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one. Theacetate radical formation was effected at 60° to 65° C. to obtain4-tetradecylaminoethyl-4-aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₂₄ H₄₅ O₃ N₃ ; Calculated (%)--C 68.05, H 10.71, N9.92, Found (%)--C 68.09, H 10.74, N 9.90.

IR spectrum--1635 cm⁻¹ ##STR64##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 54

Into an apparatus similar to that in Example 1, were charged 339.5 g (1mole) of N-(2-hydroxy)hexadecyldiethylenetriamine and 130.1 g (1 mole)of ethyl 3-formylpropionate. At 135° to 140° C., 18 g of water and 46 gof ethanol were distilled off to obtain4-(2-hydroxyhexadecyl)aminoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₂₄ H₄₃ O₂ N₃ ; Calculated (%)--C 71.08, H 10.69, N10.36, Found (%)--C 71.11, H 10.70, N 10.34.

Amine Value: 276.6 (theoretical 276.7).

IR spectrum: 1618 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 405.5 g (1 mole) of4-(2-hydroxyhexadecyl)aminoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-onedissolved in 300 g of isopropyl alcohol, was added a solution of 132.6 g(1 mole) of potassium monochloroacetate dissolved in 600 g of water. Theacetate radical formation was effected at 50° to 60° C. to obtain4-(2-hydroxyhexadecyl)aminoethyl-4-aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₂₆ H₄₅ O₄ N₃ ; Calculated (%)--C 67.37, H 9.79, N9.06, Found (%)--C 67.36, H 9.78, N 9.06.

IR spectrum--1640 cm⁻¹ ##STR65##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.08 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 55

Into an apparatus similar to that in Example 1, were charged 310.1 g (1mole) of N-(9-octadecenyl)ethylenediamine and 158.2 g (1 mole) of butyl3-formylpropionate. At 150° C. and under a reduced pressure of 50 mmHg,18 g of water and 74 g of butanol were distilled off to obtain4-(9-octadecenyl)-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₂₄ H₄₄ ON₂ ; Calculated (%)--C 76.53, H 11.79, N7.43, Found (%)--C 76.55, H 11.80, N 7.45.

Amine value--149.0 (theoretical 149.0).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 94.5 g (1 mole) of monochloroacetic aciddissolved in 500 g of water, was added dropwise 376.6 g (1 mole) of theformed 4-(9-octadecenyl)-2,3,6,7-tetrahydro-1,4-diazocin-5-one. Aftermixing at 65° to 75° C. and further addition of 56.1 g (1 mole) ofpotassium hydroxide, the reaction was allowed to proceed at the sametemperature to obtain4-(9-octadecenyl)-4-aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₂₆ H₄₆ O₃ N₂ ; Calculated (%)--C 71.84, H 10.67, N6.44, Found (%)--C 71.80, H 10.65, N 6.46.

IR spectrum--1635 cm⁻¹ ##STR66##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 56

Into an apparatus similar to that in Example 1, were charged 103.1 g (1mole) of diethylenetriamine and 144.2 g (1 mole) of propyl3-formylpropionate. At 140° to 145° C., 18 g of water and 60 g of propylalcohol were distilled off. Then, after adding 144.2 g (1 mole) ofoctylic acid, the reaction was allowed to proceed at 150° to 155° C. todistil off 18 g of water, obtaining4-octamidoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₁₆ H₂₉ O₂ N₃ ; Calculated (%)--C 65.09, H 9.90, N14.23, Found (%)--C 65.08, H 9.89, N 14.24.

Amine value--192.2 (theoretical 190.1).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 107.6 g (1 mole) of monochloropropionicacid dissolved in 600 g of water, was added dropwise 295.2 g (1 mole) of4-octamidoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one. After mixing at70° to 80° C. and adding 40.0 g (1 mole) of sodium hydroxide, thereaction was allowed to proceed at the same temperature to obtain4-octamidoethyl-4-aza-1-azoniacyclooct-8-en-5-one-1-propionate.

Elementary analysis: C₁₉ H₃₃ O₄ N₃ ; Calculated (%)--C 62.09, H 9.06, N11.43, Found (%)--C 62.05, H 9.04, N 11.43.

IR spectrum--1635 cm⁻¹ ##STR67##

NMR spectrum-- ##STR68## methyne proton 2.25 ppm (δ, DSS standard, 50MHz).

EXAMPLE 57

Into an apparatus similar to that in Example 1, were charged 104.2 g (1mole) of N-hydroxyethylethylenediamine and 116.1 g (1 mole) of methyl3-formylpropionate. At 130° C., 18 g of water and 32 g of methanol weredistilled off. After adding 340.5 g (1 mole) of behenic acid,esterification was carried out at 210° to 220° C. to obtain4-behenoyloxyethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₃₀ H₅₄ O₃ N₂ ; Calculated (%)--C 73.43, H 11.09, N5.71, Found (%)--C 73.41, H 11.09, N 5.74.

Amine value--115.0 (theoretical 114.3).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide), 1735 cm⁻¹(ν_(C)═O, ester).

Subsequently, 490.7 g (1 mole) of4-behenoyloxyethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one and 116.5 g (1mole) of sodium monochloroacetate were allowed to react in the presenceof 600 g of water and 600 g of ethanol to obtain4-behenoyloxyethyl-4-aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₃₂ H₅₆ O₅ N₂ ; Calculated (%)--C 70.04, H 10.28, N5.10, Found (%)--C 70.08, H 10.31, N 5.08.

IR spectrum--1635 cm⁻¹ ##STR69##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.13 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 58

Into an apparatus similar to that in Example 1, were charged 299.5 g (1mole) of N-tetradecyldiethylenetriamine and 130.1 g (1 mole) of methyl2-formyl-2-methylpropionate. At 140° to 145° C., 18 g of water and 32 gof methanol were distilled off to obtain4-tetradecylaminoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₃ H₄₅ ON₃ ; Calculated (%)--C 72.76, H 11.96, N11.06, Found (%)--C 72.74, H 11.98, N 11.06.

Amine value--296.0 (theoretical 295.6).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 107.6 g (1 mole) of monochloropropionicacid dissolved in 600 g of water, was added dropwise 379.6 g (1 mole) of4-tetradecylaminoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one. Aftermixing at 70° to 75° C. and adding 40.0 g (1 mole) of sodium hydroxide,the reaction was allowed to proceed at the same temperature to obtain4-tetradecylaminoethyl-6,6-dimethyl-1-azonia-4-azacyclohept-7-en-5-one-1-propionate.

Elementary analysis: C₂₆ H₄₉ O₃ N₃ ; Calculated (%)--C 69.14, H 10.94, N9.30, Found (%)--C 69.16, H 10.96, N 9.33.

IR spectrum--1645 cm⁻¹ ##STR70##

NMR spectrum-- ##STR71## methyne proton 2.42 ppm (δ, DSS standard, 50MHz).

EXAMPLE 59

Into an apparatus similar to that in Example 1, were charged 339.5 g (1mole) of N-(2-hydroxy)hexadecyldiethylenetriamine and 144.2 g (1 mole)of ethyl 2-formyl-2-methylpropionate. At 140° to 160° C., 18 g of waterand 46 g of ethanol were distilled off to obtain4-(2-hydroxyhexadecyl)aminoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₅ H₄₅ O₂ N₃ ; Calculated (%)--C 71.55, H 10.82, N10.01, Found (%)--C 71.59, H 10.83, N 10.00.

Amine value--267.5 (theoretical 267.3)

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 419.7 g (1 mole) of4-(2-hydroxyhexadecyl)aminoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-onedissolved in 300 g of tetrahydrofuran, was added a solution of 177.0 g(1 mole) of potassium monobromoacetate dissolved in 800 g of water. Theacetate radical formation was effected at 60° to 70° C. to obtain4-(2-hydroxyhexadecyl)aminoethyl-6,6-dimethyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₇ H₄₇ O₄ N₃ ; Calculated (%)--C 67.89, H 9.92, N8.79, Found (%)--C 67.91, H 9.90, N 8.81.

IR spectrum--1645 cm⁻¹ ##STR72##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.12 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 60

Into an apparatus similar to that in Example 1, were charged 313.5 g (1mole) of N-monotetradecylaminoethylpropylenediamine and 158.2 g (1 mole)of isopropyl 2-formyl-2-methylpropionate. At 150° to 155° C., 18 g ofwater and 60 g of isopropyl alcohol were distilled off to obtain1-tetradecylaminoethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-one.

Elementary analysis: C₂₄ H₄₇ ON₃ ; Calculated (%)--C 73.32, H 12.04, N10.67, Found (%)--C 73.30, H 12.00, N 10.69.

Amine value--285.1 (theoretical 285.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 107.6 g (1 mole) of monochloropropionicacid dissolved in 700 g of water, was added dropwise 393.6 g (1 mole) of1-tetradecylaminoethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-one.After mixing at 70° to 80° C. and adding 56.1 g (1 mole) of potassiumhydroxide, the reaction was allowed to proceed at the same temperatureto obtain1-tetradecylaminoethyl-3,3-dimethyl-1-aza-5-azoniacyclooct-4-en-2-one-5-propionate.

Elementary analysis: C₂₇ H₅₁ O₃ N₃ ; Calculated (%)--C 69.64, H 11.04, N9.02, Found (%)--C 69.60, H 11.03, N 9.04.

IR spectrum--1630 cm⁻¹ ##STR73##

NMR spectrum-- ##STR74## metyne proton 2.38 ppm (δ, DSS standard, 50MHz).

EXAMPLE 61

Into an apparatus similar to that in Example 1, were charged 353.5 g (1mole) of N-mono(2-hydroxy)hexadecylaminoethylpropylenediamine and 172.2g (1 mole) of butyl 2-formyl-2-methylpropionate. At 160° to 165° C. andunder a reduced pressure of 70 mmHg, 18 g of water and 74 g of butanolwere distilled off to obtain1-(2-hydroxyhexadecyl)aminoethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-one.

Elementary analysis: C₂₆ H₄₇ O₂ N₃ ; Calculated (%)--C 72.01, H 10.93, N9.68, Found (%)--C 71.98, H 10.90, N 9.68.

Amine value--258.9 (theoretical 258.7).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 433.7 g (1 mole) of1-(2-hydroxyhexadecyl)aminoethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-onedissolved in 300 g of ethanol, was added a solution of 116.5 g (1 mole)of sodium monochloroacetate dissolved in 600 g of water. The acetateradical formation was effected at 60° to 70° C. to obtain1-(2-hydroxyhexadecyl)aminoethyl-3,3-dimethyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₈ H₄₉ O₄ N₃ ; Calculated (%)--C 68.40, H 10.05, N8.54, Found (%)--C 68.40, H 10.08, N 8.55.

IR spectrum--1640 cm⁻¹ ##STR75##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.11 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 62

Into an apparatus similar to that in Example 1, were charged 364.2 g (1mole) of N-nonylphenylpoly(2 moles) oxyethyleneoxyethyl-1,3-propylenediamine and 130.1 g (1 mole) of methyl 2-formyl-2-methylpropionate. At100° C. and under a reduced pressure of 100 mmHg, 18 g of water and 32 gof methanol were distilled off to obtain 1-nonylphenylpoly(2moles)oxyethyleneoxyethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-one.

Elementary analysis: C₂₇ H₄₄ O₃ N₂ ; Calculated (%)--C 72.93, H 9.98, N6.30, Found (%)--C 72.90, H 9.97, N 6.34.

Amine value--125.0 (theoretical 126.2).

IR spectrum--1620 cm⁻¹ (ν_(C)═N), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 161.0 g (1 mole) of sodiummonobromoacetate dissolved in 500 g of water, was added dropwise 444.7 g(1 mole) of 1-nonylphenylpoly(2moles)oxyethyleneoxyethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-one.The acetate radical formation was effected at 60° to 70° C. to obtain1-nonylphenylpoly(2moles)oxyethyleneoxyethyl-3,3-dimethyl-1-aza-5-azoniacyclooct-4-en-2-one-5-acetate.

Elementary analysis: C₂₈ H₄₆ O₅ N₂ ; Calculated (%)--C 68.53, H 9.46, N5.71, Found (%)--C 68.57, H 9.48, N 5.71.

IR spectrum--1635 cm⁻¹ ##STR76##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 63

Into an apparatus similar to that in Example 1, were charged 230.1 g (1mole) of N-octoxypropylethylenediamine and 130.1 g (1 mole) of methyl2-formyl-2-methylpropionate. At 130° to 135° C., 18 g of water and 32 gof methanol were distilled off to obtain4-octoxypropyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₁₈ H₃₄ O₂ N₂ ; Calculated (%)--C 69.63, H 11.05, N9.02, Found (%)--C 69.60, H 11.04, N 9.05.

Amine value--180.7 (theoretical 180.7).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 310.5g (1 mole) of 4-octoxypropyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one.The acetate radical formation was effected at 50° to 60° C. to obtain4-oxtoxypropyl-6,6-dimethyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₀ H₃₆ O₄ N₂ ; Calculated (%)--C 65.18, H 9.85, N7.60, Found (%)--C 65.20, H 9.85, N 7.61.

IR spectrum--1635 cm⁻¹ ##STR77##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.18 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 64

Into an apparatus similar to that in Example 1, were charged 103.1 g (1mole) of diethylenetriamine and 144.2 g (1 mole) of ethyl2-formyl-2-methylpropionate. At 140° C., 18 g of water and 46 g ofmethanol were distilled off. Then, after addition of 312.5 g (1 mole) ofmethyl ricinoleate, amide formation was carried out at 170° to 180° C.under a reduced pressure of 70 mmHg to distil off 32 g of methanol,yielding 4-ricinolamidoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one.

Elementary analysis: C₂₇ H₄₉ O₃ N₃ ; Calculated (%)--C 69.94, H 10.65, N9.06, Found (%)--C 69.98, H 10.66, N 9.05.

Amine value--120.6 (theoretical 121.0).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 94.5 g (1 mole) of monochloroacetic aciddissolved in 500 g of water, was added dropwise 463.7 g (1 mole) of4-ricinolamidoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one. Aftermixing at 50° to 60° C. and adding 40.0 g (1 mole) of sodium hydroxide,the reaction was allowed to proceed at the same temperature to obtain4-ricinolamidoethyl-6,6-dimethyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.

Elementary analysis: C₂₉ H₅₁ O₅ N₃ ; Calculated (%)--C 66.76, H 9.85, N8.05, Found (%)--C 66.78, H, 9.85, N 8.05.

IR spectrum--1630 cm⁻¹ ##STR78##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 65

Into an apparatus similar to that in Example 1, where charged 299.5 g (1mole) of N-tetradecyldiethylenetriamine and 130.1 g (1 mole) of methyl3-formyl-2-methylpropionate. At 145° to 150° C., 18 g of water and 32 gof methanol were distilled off to obtain4-tetradecylaminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₂₃ H₄₅ ON₃ ; Calculated (%)--C 72.76, H 11.96, N11.06, Found (%)--C 72.73, H 11.94, N 11.08.

Amine value--295.9 (theoretical 295.6).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 107.6 g (1 mole) of monochloropropionicacid dissolved in 600 g of water, was added dropwise 379.6 g (1 mole) of4-tetradecylaminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.After mixing at 70° C. to 80° C. and adding 56.1 g (1 mole) of potassiumhydroxide, the reaction was allowed to proceed at the same temperatureto obtain4-tetradecylaminoethyl-6-methyl-4-aza-1-azoniacyclooct-8-en-5-one-1-propionate.

Elementary analysis: C₂₆ H₄₉ O₃ N₃ ; Calculated (%)--C 69.14, H 10.94, N9.30, Found (%)--C 69.14, H 10.95, N 9.32.

IR spectrum--1640 cm⁻¹ ##STR79##

NMR spectrum-- ##STR80## methyne proton 2.40 ppm (δ, DSS standard, 50MHz).

EXAMPLE 66

Into an apparatus similar to that in Example 1, were charged 339.5 g (1mole) of N-(2-hydroxy)hexadecyldiethylenetriamine and 144.2 g (1 mole)of ethyl 3-formyl-2-methylpropionate. At 140° to 160° C., 18 g of waterand 46 g of ethanol were distilled off to obtain4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₂₅ H₄₅ O₂ N₃ ; Calculated (%)--C 71.55, H 10.82, N10.01, Found (%)--C 71.51, H 10.80, N 10.04.

Amine value--267.7 (theoretical 267.3).

IR spectrum--1615 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 419.7 g (1 mole) of4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-onedissolved in 200 g of dioxane, was added a solution of 116.5 g (1 mole)of sodium monochloroacetate dissolved in 800 g of water. The acetateradical formation was effected at 60° to 70° C. to obtain4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-4-aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₂₇ H₄₇ O₄ N₃ ; Calculated (%)--C 67.89, H 9.92, N8.79, Found (%)--C 67.92, H 9.94, N 8.80.

IR spectrum--1645 cm⁻¹ ##STR81##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.10 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 67

Into an apparatus similar to that in Example 1, were charged 338.5 g (1mole) of N-methylbenzylpoly(2 moles)oxypropyleneoxypropylethylenediamineand 172.2 g (1 mole) of butyl 3-formyl-2-methylpropionate. At 150° to160° C., 18 g of water and 74 g of butanol to obtain4-methylbenzylpoly(2moles)oxypropyleneoxypropyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₂₄ H₃₈ O₄ N₂ ; Calculated (%)--C 68.86, H 9.15, N6.69, Found (%)--C 68.80, H 9.14, N 6.71.

Amine value--135.0 (theoretical 134.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 600 g of water, was added dropwise 418.5g (1 mole) of4-methylbenzylpoly(2moles)oxypropyleneoxypropyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.The acetate radical formation was effected at 50° to 60° C. to obtain4-methylbenzylpoly(2moles)oxypropyleneoxypropyl-6-methyl-4-aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₂₆ H₄₀ O₆ N₂ ; Calculated (%)--C 65.53, H 8.46, N5.87, Found (%)--C 65.58, H 8.46, N 5.86.

IR spectrum--1630 cm⁻¹ ##STR82##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.07 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 68

Into an apparatus similar to that in Example 1, were charged 118.2 g (1mole) of N-hydroxypropylethylenediamine and 158.2 g (1 mole) ofisopropyl 3-formyl-2-methylpropionate. From the apparatus, 18 g of waterand 60 g of isopropyl alcohol were distilled off. Then, 340.5 g (1 mole)of behenic acid was charged and 18 g of water was distilled off at 180°C. and under a reduced pressure of 70 mmHg to obtain4-behenoyloxypropyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₃₂ H₅₈ O₃ N₂ ; Calculated (%)--C 74.08, H 11.27, N53.97, Found (%)--C 74.10, H 11.27, N 54.01.

Amine value--108.5 (theoretical 108.1).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1660 cm⁻¹ (ν_(C)═O, amide), 1735 cm⁻¹(ν_(C)═O, ester).

Subsequently, to a solution of 518.1 g (1 mole) of4-behenoyloxypropyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-onedissolved in 600 g of tetrahydrofuran, was added dropwise a solution of116.5 g (1 mole) of sodium monochloroacetate dissolved in 600 g ofwater. The acetate radical formation was effected at 70° to 80° C. toobtain4-behenoyloxypropyl-6-methyl-4aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₃₄ H₆₀ O₅ N₂ ; Calculated (%)--C 70.79, H 10.49, N4.85, Found (%)--C 70.78, H 10.47, N 4.85.

IR spectrum--1640 cm⁻¹ ##STR83##

NMR spectrum--N⁺ -CH₂ COO⁻ proton 2.06 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 69

Into an apparatus similar to that in Example 1, were charged 465.7 g (1mole) of N-nonylphenoxy(2-hydroxy)propyltetraethylenepentamine and 144.2g (1 mole) of ethyl 3-formyl-2-methylpropionate. At 120° to 130° C. andunder a reduced pressure of 100 mmHg, 18 g of water and 46 g of ethanolwere distilled off to obtain4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.

Elementary analysis: C₃₁ H₅₅ O₃ N₅ ; Calculated (%)--C 68.22, H 10.15, N12.83, Found (%)--C 68.20, H 10.15, N 12.80.

Amine value--410.0 (theoretical 411.2).

IR spectrum--1610 cm⁻¹ (ν_(C)═N), 1655 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 177.0 g (1 mole) of potassiummonobromoacetate dissolved in 1,000 g of water, was added dropwise 545.7g (1 mole) of4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.The acetate radical formation was effected at 55° to 60° C. to obtain4-nonylphenoxy(2-hydroxy)propylaminoethylaminoethylaminoethyl-6-methyl-4-aza-1-azoniacyclooct-8-en-5-one-1-acetate.

Elementary analysis: C₃₃ H₅₇ O₅ N₅ ; Calculated (%)--C 65.63, H 9.52, N11.59, Found (%)--C 65.50, H 9.49, N 11.59.

IR spectrum--1645 cm⁻¹ ##STR84##

NMRS spectrum--N⁺ -CH₂ COO⁻ proton 2.11 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 70

Into an apparatus similar to that in Example 1, were charged 429.6 g (1mole) of a monotridecoxyethyl derivative of a 1,3-propanediaminepoly(3moles on the average)ethyleneimine adduct and 130.1 g (1 mole) of methyl3-formyl-2-methylpropionate. At 150° to 155° C., 18 g of water and 32 gof methanol were distilled off to synthesize an N-alkylazaalkenelactam.

Elementary analysis: C₂₉ H₅₉ O₂ N₅ ; Calculated (%)--C 68.32, H 11.67, N13.73, Found (%)--C 68.36, H 11.69, N 13.70.

Amine value--439.1 (theoretical 440.2).

IR spectrum--1610 cm⁻¹ (ν_(C)═O), 1650 cm⁻¹ (ν_(C)═O, amide).

Subsequently, to a solution of 116.5 g (1 mole) of sodiummonochloroacetate dissolved in 1,000 g of water, was added dropwise509.8 g (1 mole) of the formed N-alkylazaalkenelactam. The reaction wasallowed to proceed at 60° to 70° C. to obtain the compound having anacetate radical.

Elementary analysis: C₃₁ H₆₁ O₄ N₅ ; Calculated (%)--C 65.57, H 10.83, N12.33, Found (%)--C 65.57, H 10.80, N 12.33.

IR spectrum--1635 cm⁻¹ ##STR85##

NMR spectrum--N⁺ -CH₂ COO proton 2.11 ppm (δ, DSS standard, 50 MHz).

EXAMPLE 71

Below are described the antibacterial activities of the compounds in thecompositions according to this invention. The results of antibacterialactivity tests on the N-alkyl-substituted azaalkenelactams and theirderivatives having a carboxylate radical of Examples 1 to 70 were asshown in Tables 1 to 3.

The testing method complied with the standard method of Japan Sociaty ofChemotherapy. Aqueous solutions of each compound in distilled water invarious concentrations were added to the following bacteria cultivatedin heart infusion agar media at 37° C. and the minimum concentration ofthe compound to inhibit completely the growth of test bacteria in 24hours (hereinafter referred to as MIC) was examined: Escherichia coliNIHJ, Staphylococcus aureus FDA 209P, Desulfovibrio desulfuricans IFO3699, Pseudomonas aeruginosa IFO 3445, Bacillus subtilis ATCC 6633,Pasteurella multocida, almonella typhimurium, Staphylococcusepidermidis, and Streptococcus faecalis, wherein Desulfovibriodesulfuricans is a bacterium which generates hydrogen sulfide and, forthis reason, acts to cause corrosion of metals.

EXAMPLE 72

In Tables 4 and 5, are further shown the results of tests for the metalcorrosion inhibiting performance of the systems comprising an automobilebrake fluid A of the following composition and, incorporated therein,each 0.25% by weight of N-alkyl-substituted azaalkenelactams or theirderivatives having a carboxylate radical obtained in Examples 1 to 70.

Brake fluid composition A;

Trioxyethylene glycol monomethyl ether--35 parts

Trioxyethylene glycol monoethyl ether--20 parts

Trioxyethylene glycol monobutyl ether--20 parts

Poly(20 moles on the average)oxyethylene glycol monomethyl ether--15parts

Poly(10 moles on the average)oxyethylene-poly(10 moles on theaverage)oxypropylene glycol monoethyl ether--10 parts

The testing method conformed to Japanese Industrial Standards JIS K2233: a series of metal plates of tin-plate, steel, aluminum, cast iron,brass and copper connected to each other in the order indicated wasimmersed in the brake fluid system being tested, then left standing at100°±2° C. for 120±2 hours and the weight difference per unit areabefore and after the test was examined.

As for the reference substances, laurylbutylamine andoleylaminopropyloleamide were selected for the N-alkyl-substitutedazaalkenelactam, and lauryldimethylbetaine and1-hydroxyethyl-2-undecylimidazolineumbetaine were selected for thederivatives having an organic acid, e.g. a carboxylate radical of saidlactam. These were subjected to the antibacterial activity test and themetal corrosion test in a similar manner to that described above.

                                      TABLE 1                                     __________________________________________________________________________    Antibacterial Activity of Azaalkenelactams                                    with Long chain hydrocarbon radical                                                     MIC (μg/ml)                                                      Sample    Esherichia coli                                                                       Staphylococcus aureus                                                                    Desulfovibrio desul-                             (Azaalkenelactam)                                                                       HIHJ    FDA209P    furicans IFO 13699                               __________________________________________________________________________    Example 1 1600    50         6.25                                             Example 2 25      12.5       12.5                                             Example 3 1600    50         6.25                                             Example 4 800     25         12.5                                             Example 5 3200    12.5       6.25                                             Example 6 50      12.5       25                                               Example 7 200     12.5       12.5                                             Example 8 800     50         50                                               Example 9 25      12.5       6.25                                             Example 10                                                                              1600    50         6.25                                             Example 11                                                                              1600    100        6.25                                             Example 12                                                                              1600    100        12.5                                             Example 13                                                                              1600    100        12.5                                             Example 14                                                                              1600    100        12.5                                             Example 15                                                                              1600    50         6.25                                             Example 16                                                                              50      100        25                                               Example 17                                                                              1600    50         25                                               Example 18                                                                              1600    100        12.5                                             Example 19                                                                              400     50         25                                               Example 20                                                                              800     50         12.5                                             Example 21                                                                              800     50         25                                               Example 22                                                                              800     25         12.5                                             Example 23                                                                              25      25         50                                               Example 24                                                                              800     200        25                                               Example 25                                                                              1600    200        50                                               Example 26                                                                              50      50         12.5                                             Example 27                                                                              25      12.5       6.25                                             Example 28                                                                              25      25         12.5                                             Example 29                                                                              25      6.25       3.12                                             Example 30                                                                              25      12.5       3.12                                             Example 31                                                                              400     50         50                                               Example 32                                                                              800     200        25                                               Example 33                                                                              400     25         25                                               Example 34                                                                              25      3.12       3.12                                             Example 35                                                                              6.25    1.56       1.56                                             Example 36                                                                              50      12.5       25                                               Example 37                                                                              25      6.25       6.25                                             Example 38                                                                              50      12.5       25                                               Example 39                                                                              200     25         50                                               Example 40                                                                              6.25    1.56       1.56                                             Example 41                                                                              25      3.12       3.12                                             Example 42                                                                              400     12.5       6.25                                             Example 43                                                                              400     12.5       12.5                                             Example 44                                                                              800     50         25                                               Example 45                                                                              800     100        50                                               Example 46                                                                              25      6.25       6.25                                             Example 47                                                                              200     50         50                                               Example 48                                                                              12.5    3.12       3.12                                             Example 49                                                                              25      3.12       3.12                                             Example 50                                                                              50      25         50                                               Example 51                                                                              100     25         12.5                                             Example 52                                                                              100     100        50                                               Example 53                                                                              6.25    1.56       3.12                                             Example 54                                                                              6.25    6.25       6.25                                             Example 55                                                                              200     100        50                                               Example 56                                                                              100     200        50                                               Example 57                                                                              100     100        12.5                                             Example 58                                                                              6.25    3.12       3.12                                             Example 59                                                                              25      6.25       3.12                                             Example 60                                                                              12.5    6.25       6.25                                             Example 61                                                                              25      6.25       6.25                                             Example 62                                                                              200     100        50                                               Example 63                                                                              400     100        50                                               Example 64                                                                              400     200        25                                               Example 65                                                                              12.5    3.12       6.25                                             Example 66                                                                              25      12.5       12.5                                             Example 67                                                                              400     200        50                                               Example 68                                                                              200     100        25                                               Example 69                                                                              200     200        50                                               Example 70                                                                              200     100        25                                               Laurylbutylamide                                                                        10000 or more                                                                         10000 or more                                                                            400                                              Oleylaminopropyl                                                                        10000 or more                                                                         10000 or more                                                                            100                                              oleamide                                                                      __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Antibacterial Activity of Derivatives having a carboxylate                    radical of Azaalkenelactams with long chain hydrocarbon radical                                MIC (μg/ml)                                                                                 Desulfovibrio                                                Esherichia coli                                                                       Staphylococcus                                                                         desulfuricans                               Sample           NIHJ    aureus FDA 209P                                                                        IFO 13699                                   __________________________________________________________________________    Example 1,                                                                           Compound having an                                                                      3200    50       12.5                                               acetate radical                                                        Example 2,                                                                           Compound having an                                                                      100     50       12.5                                               acetate radical                                                        Example 3,                                                                           Compound having an                                                                      3200    100      12.5                                               acetate radical                                                        Example 4,                                                                           Compound having an                                                                      800     12.5     12.5                                               acetate radical                                                        Example 5,                                                                           Compound having an                                                                      3200    100      12.5                                               acetate radical                                                        Example 6,                                                                           Compound having an                                                                      200     25       25                                                 acetate radical                                                        Example 7,                                                                           Compound having an                                                                      200     12.5     25                                                 acetate radical                                                        Example 8,                                                                           Compound having an                                                                      1600    50       50                                                 acetate radical                                                        Example 9,                                                                           Compound having an                                                                      100     50       12.5                                               acetate radical                                                        Example 10,                                                                          Compound having an                                                                      3200    25       12.5                                               acetate radical                                                        Example 11,                                                                          Compound having an                                                                      3200    50       25                                                 acetate radical                                                        Example 12,                                                                          Compound having an                                                                      3200    400      25                                                 acetate radical                                                        Example 13,                                                                          Compound having an                                                                      3200    200      25                                                 acetate radical                                                        Example 14,                                                                          Compound having an                                                                      3200    400      25                                                 acetate radical                                                        Example 15,                                                                          Compound having an                                                                      3200    200      12.5                                               acetate radical                                                        Example 16,                                                                          Compound having an                                                                      100     400      50                                                 acetate radical                                                        Example 17,                                                                          Compound having an                                                                      3200    100      50                                                 acetate radical                                                        Example 18,                                                                          Compound having an                                                                      3200    100      25                                                 acetate radical                                                        Example 19,                                                                          Compound having an                                                                      800     50       50                                                 acetate radical                                                        Example 20,                                                                          Compound having an                                                                      1600    50       25                                                 acetate radical                                                        Example 21,                                                                          Compound having an                                                                      1600    50       25                                                 acetate radical                                                        Example 22,                                                                          Compound having an                                                                      3200    12.5     12.5                                               acetate radical                                                        Example 23,                                                                          Compound having an                                                                      100     800      50                                                 acetate radical                                                        Example 24,                                                                          Compound having an                                                                      3200    800      50                                                 acetate radical                                                        Example 25,                                                                          Compound having an                                                                      3200    100      50                                                 acetate radical                                                        Example 26,                                                                          Compound having an                                                                      200     100      6.25                                               acetate radical                                                        Example 27,                                                                          Compound having an                                                                      100     25       6.25                                               acetate radical                                                        Example 28,                                                                          Compound having an                                                                      100     50       12.5                                               acetate radical                                                        Example 29,                                                                          Compound having an                                                                       50     25       3.12                                               acetate radical                                                        Example 30,                                                                          Compound having an                                                                        50    25       6.25                                               acetate radical                                                        Example 31,                                                                          Compound having an                                                                      800     100      25                                                 acetate radical                                                        Example 32,                                                                          Compound having an                                                                      800     100      50                                                 acetate radical                                                        Example 33,                                                                          Compound having a                                                                       800     25       12.5                                               propionate radical                                                     Example 34,                                                                          Compound having an                                                                      100     12.5     6.25                                               acetate radical                                                        Example 35,                                                                          Compound having an                                                                      100     3.12     3.12                                               acetate radical                                                        Example 36,                                                                          Compound having an                                                                      100     12.5     50                                                 acetate radical                                                        Example 37,                                                                          Compound having a                                                                       100     6.25     6.25                                               propionate radical                                                     Example 38,                                                                          Compound having an                                                                      100     12.5     25                                                 acetate radical                                                        Example 39,                                                                          Compound having an                                                                      400     50       50                                                 acetate radical                                                        Example 40,                                                                          Compound having an                                                                      100     6.25     6.25                                               acetate radical                                                        Example 41,                                                                          Compound having an                                                                      100     12.5     3.12                                               acetate radical                                                        Example 42,                                                                          Compound having an                                                                      800     25       25                                                 acetate radical                                                        Example 43,                                                                          Compound having an                                                                      800     25       25                                                 acetate radical                                                        Example 44,                                                                          Compound having an                                                                      1600    50       25                                                 acetate radical                                                        Example 45,                                                                          Compound having an                                                                      1600    100      50                                                 acetate radical                                                        Example 46,                                                                          Compound having an                                                                       50     12.5     6.25                                               acetate radical                                                        Example 47,                                                                          Compound having an                                                                      200     50       50                                                 acetate radical                                                        Example 48,                                                                          Compound having a                                                                       100     6.25     6.25                                               propionate radical                                                     Example 49,                                                                          Compound having an                                                                      100     12.5     6.25                                               acetate radical                                                        Example 50,                                                                          Compound having an                                                                      100     50       50                                                 acetate radical                                                        Example 51,                                                                          Compound having an                                                                      100     50       25                                                 acetate radical                                                        Example 52,                                                                          Compound having an                                                                      400     200      50                                                 acetate radical                                                        Example 53,                                                                          Compound having an                                                                      100     3.12     6.25                                               acetate radical                                                        Example 54,                                                                          Compound having an                                                                      100     12.5     6.25                                               acetate radical                                                        Example 55,                                                                          Compound having an                                                                      400     200      50                                                 acetate radical                                                        Example 56,                                                                          Compound having a                                                                       200     400      50                                                 propionate radical                                                     Example 57,                                                                          Compound having an                                                                      200     100      12.5                                               acetate radical                                                        Example 58,                                                                          Compound having a                                                                       100     6.25     6.25                                               propionate radical                                                     Example 59,                                                                          Compound having an                                                                      200     12.5     6.25                                               acetate radical                                                        Example 60,                                                                          Compound having a                                                                       100     12.5     6.25                                               propionate radical                                                     Example 61,                                                                          Compound having an                                                                      100     12.5     12.5                                               acetate radical                                                        Example 62,                                                                          Compound having an                                                                      400     100      50                                                 acetate radical                                                        Example 63,                                                                          Compound having an                                                                      800     200      50                                                 acetate radical                                                        Example 64,                                                                          Compound having an                                                                      1600    400      50                                                 acetate radical                                                        Example 65,                                                                          Compound having a                                                                       100     6.25     6.25                                               propionate radical                                                     Example 66,                                                                          Compound having an                                                                      100     25       25                                                 acetate radical                                                        Example 67,                                                                          Compound having an                                                                      800     400      25                                                 acetate radical                                                        Example 68,                                                                          Compound having an                                                                      800     200      25 - acetate radical                        Example 69,                                                                          Compound having an                                                                      400     200      50                                                 acetate radical                                                        Example 70,                                                                          Compound having an                                                                      400     200      25                                                 acetate radical                                                        Lauryldimethylbetaine                                                                          10000 or more                                                                         10000 or more                                                                          1600                                        1-hydroxyethyl-2-undecylimi-                                                                   10000 or more                                                                         3600     400                                         dazoliniumbetaine                                                             __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________    Antibacterial activity of Azaalkenelactams with long chain hydrocarbon        radical and their derivatives having an organic acid radical                                  MIC (μg/ml)                                                                              Paste-                                                                            Salmo-                                                                            Staphylo-                                               Pseudomonas                                                                          Bacillus                                                                             urella                                                                            nella                                                                             coccus                                                                             Strepto-                           aruginosa       subtilis                                                                             multo- typhi-                                                                            epider-                                                                           coccus                                  Sample          IFO 3443                                                                             ATCC 6633                                                                            cida                                                                              nurium                                                                            midis                                                                              faecalis                           __________________________________________________________________________    Example 2,                                                                           Azaalkene-                                                                             100    12.5   <1.56                                                                             3.12                                                                              1.56 12.5                                      lactam                                                                 Example 9,                                                                           Azaalkene-                                                                             100    25      3.12                                                                             6.25                                                                              6.25 12.5                                      lactam                                                                 Example 9,                                                                           Compound having                                                                        200    50     <1.56                                                                             6.25                                                                              12.5 12.5                                      an acetate                                                                    radical                                                                Example 29,                                                                          Azaalkene-                                                                             100    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 34,                                                                          Azaalkene-                                                                             100    3.12   <1.56                                                                             3.12                                                                              <1.56                                                                              6.25                                      lactam                                                                 Example 35,                                                                          Azaalkene-                                                                              54    3.12   <1.56                                                                             1.56                                                                              <1.56                                                                              3.12                                      lactam                                                                 Example 35,                                                                          Compound having                                                                        100    12.5    3.12                                                                             6.25                                                                              3.12 6.25                                      an acetate                                                                    radical                                                                Example 40,                                                                          Azaalkene-                                                                              50    3.12   <1.56                                                                             3.12                                                                              < 1.56                                                                             3.12                                      lactam                                                                 Example 41,                                                                          Azaalkene-                                                                             100    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 48,                                                                          Azaalkene-                                                                              50    6.25   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 49,                                                                          Azaalkene-                                                                             200    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 53,                                                                          Azaalkene-                                                                             100    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 54,                                                                          Azaalkene-                                                                             200    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 58,                                                                          Azaalkene-                                                                              50    3.12   <1.56                                                                             1.56                                                                              <1.56                                                                              3.12                                      lactam                                                                 Example 59,                                                                          Azaalkene-                                                                             100    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 60,                                                                          Azaalkene-                                                                             100    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 61,                                                                          Azaalkene-                                                                             200    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 65,                                                                          Azaalkene-                                                                             100    3.12   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 Example 66,                                                                          Azaalkene-                                                                             200    6.25   <1.56                                                                             3.12                                                                              1.56 6.25                                      lactam                                                                 __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________    Metal corrosion inhibiting performance of azaalkenelactams                    with long chain hydrocarbon radical in brake fluid A                                           Test metal                                                                    Tin-      Alumi-                                                                             Cast                                                           plate                                                                              Steel                                                                              num  iron Brass                                                                              Copper                                               Weight                                                                             Weight                                                                             Weight                                                                             Weight                                                                             Weight                                                                             Weight -Sample                                                                added change change change chang                                              e change change                     Blanc (Brake fluid                                                                             -0.15                                                                              -0.20                                                                              +0.07                                                                              -0.14                                                                              -0.20                                                                              +0.18                               composition A)   mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                         __________________________________________________________________________    Example 1,                                                                              N-Alkyl sub-                                                                         0    -0.01                                                                              +0.02                                                                              -0.02                                                                              0    +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 2,                                                                              N-Alkyl sub-                                                                         0    -0.01                                                                              0    0    -0.01                                                                              0                                             stituted aza-                                                                 alkenelactam                                                        Example 3,                                                                              N-Alkyl sub-                                                                         0    0    +0.01                                                                              -0.02                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 4,                                                                              N-Alkyl sub-                                                                         -0.01                                                                              0    0    -0.01                                                                              -0.01                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 5,                                                                              N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              0    0    -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 6,                                                                              N-Alkyl sub-                                                                         0    -0.01                                                                              +0.02                                                                              -0.01                                                                              0    +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 7,                                                                              N-Alkyl sub-                                                                         0    0    +0.03                                                                              -0.01                                                                              -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 8,                                                                              N-Alkyl sub-                                                                         -0.01                                                                              -0.02                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 9,                                                                              N-Alkyl sub-                                                                         0    0    0    -0.01                                                                              -0.02                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 10,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.01                                                                              0    0    -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 11,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.03                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 12,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    0    -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 13,                                                                             N-Alkyl sub-                                                                         0    -0.02                                                                              +0.03                                                                              -0.03                                                                              -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 14,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    -0.01                                                                              -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 15,                                                                             N-Alkyl sub-                                                                         0    0    0    -0.01                                                                              0    +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 16,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.01                                                                              +0.01                                                                              0    -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 17,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 18,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    0    -0.01                                                                              -0.03                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 19,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.02                                                                              0    +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 20,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.02                                                                              +0.02                                                                              -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 21,                                                                             N-Alkyl sub-                                                                         0    -0.02                                                                              +0.01                                                                              0    -0.01                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 22,                                                                             N-Alkyl sub-                                                                         0    0    +0.01                                                                              -0.03                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 23,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    -0.01                                                                              -0.03                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 24,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              +0.01                                                                              0    -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 25,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    -0.01                                                                              -0.03                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 26,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 27,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              +0.02                                                                              0    -0.03                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 28,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              0    -0.01                                                                              -0.03                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 29,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.01                                                                              -0.01                                                                              -0.01                                                                              0                                             stituted aza-                                                                 alkenelactam                                                        Example 30,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 31,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.02                                                                              +0.01                                                                              -0.01                                                                              -0.03                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 32,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.02                                                                              +0.03                                                                              0    -0.03                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 33,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.01                                                                              -0.01                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 34,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 35,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    -0.01                                                                              0    +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 36,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.02                                                                              +0.02                                                                              -0.01                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 37,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.01                                                                              -0.01                                                                              -0.03                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 38,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.02                                                                              -0.02                                                                              -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 39,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.02                                                                              -0.01                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 40,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              +0.01                                                                              -0.01                                                                              0    0                                             stituted aza-                                                                 alkenelactam                                                        Example 41,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              0    -0.01                                                                              0    +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 42,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.01                                                                              +0.01                                                                              0    -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 43,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.01                                                                              -0.02                                                                              -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 44,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.02                                                                              -0.01                                                                              -0.02                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 45,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.02                                                                              -0.02                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 46,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 47,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.01                                                                              -0.02                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 48,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.01                                                                              -0.01                                                                              0                                             stituted aza-                                                                 alkenelactam                                                        Example 49,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 50,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.02                                                                              +0.01                                                                              0    -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 51,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.02                                                                              0    -0.01                                                                              -0.03                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 52,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 53,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.01                                                                              -0.01                                                                              -0.01                                                                              0                                             stituted aza-                                                                 alkenelactam                                                        Example 54,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    0    -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 55,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.02                                                                              -0.02                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 56,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.01                                                                              +0.02                                                                              -0.02                                                                              -0.02                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 57,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.03                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 58,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 59,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    +0.01                                                                              0    -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 60,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              0    0    -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 61,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              +0.01                                                                              -0.01                                                                              0    +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 62,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 63,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.01                                                                              +0.03                                                                              -0.02                                                                              -0.01                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 64,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              +0.02                                                                              -0.02                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 65,                                                                             N-Alkyl sub-                                                                         0    -0.01                                                                              0    -0.01                                                                              -0.01                                                                              -0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 66,                                                                             N-Alkyl sub-                                                                         0    0    +0.01                                                                              -0.01                                                                              -0.01                                                                              +0.01                                         stituted aza-                                                                 alkenelactam                                                        Example 67,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.02                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 68,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.02                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Example 69,                                                                             N-Alkyl sub-                                                                         -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.02                                                                              -0.02                                                                              +0.03                                         stituted aza-                                                                 alkenelactam                                                        Example 70,                                                                             N-Alkyl sub-                                                                         -0.01                                                                              -0.01                                                                              +0.02                                                                              -0.01                                                                              -0.01                                                                              +0.02                                         stituted aza-                                                                 alkenelactam                                                        Laurylbutyramide -0.06                                                                              -0.09                                                                              +0.06                                                                              -0.08                                                                              -0.12                                                                              +0.07                               Oleylaminopropylamide                                                                          -0.04                                                                              -0.07                                                                              +0.05                                                                              -0.04                                                                              -0.10                                                                              +0.11                               __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________    Metal corrosion inhibiting performance of derivatives having                  a carboxylate radical of azaalkenelactams with long chain                     hydrocarbon radical in brake fluid composition A                                                 Test metal                                                                    Tin       Alumi-                                                                             Cast                                                           plate                                                                              Steel                                                                              num  iron Brass                                                                              Copper                                               Weight                                                                             Weight                                                                             Weight                                                                             Weight                                                                             Weight                                                                             Weight                            Sample added       change                                                                             change                                                                             change                                                                             change                                                                             change                                                                             change                            Blanc (Brake fluid -0.15                                                                              -0.20                                                                              +0.07                                                                              -0.14                                                                              -0.20                                                                              +0.18                             composition A)     mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                                                                        mg/cm.sup.2                       __________________________________________________________________________    Example 1,                                                                              Compound having                                                                        -0.03                                                                              -0.01                                                                              0    -0.04                                                                              +0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 2,                                                                              Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.01                                                                              -0.03                                                                              -0.04                                       an acetate                                                                    radical                                                             Example 3,                                                                              Compound having                                                                        -0.01                                                                              -0.01                                                                              +0.01                                                                              0    0    0                                           an acetate                                                                    radical                                                             Example 4,                                                                              Compound having                                                                        -0.01                                                                              -0.03                                                                              +0.01                                                                              -0.03                                                                              0    0                                           an acetate                                                                    radical                                                             Example 5,                                                                              Compound having                                                                        -0.01                                                                              -0.02                                                                              0    -0.01                                                                              0    0                                           an acetate                                                                    radical                                                             Example 6,                                                                              Compound having                                                                        -0.02                                                                              -0.01                                                                              0    0    -0.01                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 7,                                                                              Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 8,                                                                              Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              0    -0.01                                                                              +0.01                                       an acetate                                                                    radical                                                             Example 9,                                                                              Compound having                                                                        -0.03                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 10,                                                                             Compound having                                                                        -0.01                                                                              -0.01                                                                              0    -0.01                                                                              0    0                                           an acetate                                                                    radical                                                             Example 11,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.02                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 12,                                                                             Compound having                                                                        -0.02                                                                              -0.01                                                                              0    -0.01                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 13,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              0    0    -0.01                                                                              +0.02                                       an acetate                                                                    radical                                                             Example 14,                                                                             Compound having                                                                        -0.03                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              0    0                                           an acetate                                                                    radical                                                             Example 15,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.02                                                                              -0.01                                                                              -0.02                                                                              +0.01                                       an acetate                                                                    radical                                                             Example 16,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              0    0                                           an acetate                                                                    radical                                                             Example 17,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              0    -0.02                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 18,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              -0.01                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 19,                                                                             Compound having                                                                        -0.02                                                                              -0.01                                                                              0    -0.01                                                                              0    0                                           an acetate                                                                    radical                                                             Example 20,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 21,                                                                             Compound having                                                                        -0.03                                                                              -0.01                                                                              0    -0.01                                                                              -0.01                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 22,                                                                             Compound having                                                                        -0.03                                                                              -0.02                                                                              +0.02                                                                              0    -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 23,                                                                             Compound having                                                                        -0.03                                                                              -0.02                                                                              0    -0.01                                                                              0    0                                           an acetate                                                                    radical                                                             Example 24,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              0    +0.01                                       an acetate                                                                    radical                                                             Example 25,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              0    0                                           an acetate                                                                    radical                                                             Example 26,                                                                             Compound having                                                                        -0.01                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              -0.02                                       an acetate                                                                    radical                                                             Example 27,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.02                                                                              -0.02                                                                              -0.02                                                                              -0.02                                       an acetate                                                                    radical                                                             Example 28,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              -0.01                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 29,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              0    -0.02                                                                              +0.01                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 30,                                                                             Compound having                                                                        -0.03                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              -0.02                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 31,                                                                             Compound having                                                                        -0.03                                                                              -0.03                                                                              +0.02                                                                              -0.04                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 32,                                                                             Compound having                                                                        -0.03                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              -0.01                                                                              +0.01                                       an acetate                                                                    radical                                                             Example 33,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              0    -0.01                                                                              -0.02                                                                              -0.01                                       a propionate                                                                  radical                                                             Example 34,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.02                                                                              -0.03                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 35,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              0    -0.01                                                                              0    0                                           an acetate                                                                    radical                                                             Example 36,                                                                             Compound having                                                                        - 0.02                                                                             -0.03                                                                              +0.02                                                                              -0.02                                                                              -0.02                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 37,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              -0.01                                                                              0                                           a propionate                                                                  radical                                                             Example 38,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              +0.02                                                                              -0.01                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 39,                                                                             Compound having                                                                        -0.01                                                                              -0.03                                                                              +0.02                                                                              -0.01                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 40,                                                                             Compound having                                                                        -0.02                                                                              -0.01                                                                              +0.02                                                                              0    -0.02                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 41,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.01                                                                              0    -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 42,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              0    0                                           an acetate                                                                    radical                                                             Example 43,                                                                             Compound having                                                                        -0.03                                                                              -0.02                                                                              +0.02                                                                              -0.03                                                                              -0.01                                                                              -0.02                                       an acetate                                                                    radical                                                             Example 44,                                                                             Compound having                                                                        -0.03                                                                              -0.01                                                                              0    -0.03                                                                              -0.01                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 45,                                                                             Compound having                                                                        -0.01                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 46,                                                                             Compound having                                                                        -0.03                                                                              -0.03                                                                              +0.02                                                                              -0.02                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 47,                                                                             Compound having                                                                        -0.03                                                                              -0.03                                                                              +0.02                                                                              -0.04                                                                              -0.02                                                                              -0.02                                       an acetate                                                                    radical                                                             Example 48,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              0    -0.02                                                                              -0.01                                                                              -0.01                                       a propionate                                                                  radical                                                             Example 49,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.01                                                                              0    -0.01                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 50,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.02                                                                              -0.03                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 51,                                                                             Compound having                                                                        -0.03                                                                              -0.03                                                                              +0.02                                                                              -0.03                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 52,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.02                                                                              0    -0.01                                                                              -0.01                                       an acetate                                                                    radical                                                             Example 53,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.01                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 54,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              -0.02                                                                              -0.02                                       an acetate                                                                    radical                                                             Example 55,                                                                             Compound having                                                                        -0.03                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 56,                                                                             Compound having                                                                        -0.02                                                                              -0.03                                                                              +0.02                                                                              -0.03                                                                              -0.01                                                                              -0.02                                       a propionate                                                                  radical                                                             Example 57,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              +0.01                                                                              -0.02                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 58,                                                                             Compound having                                                                        -0.03                                                                              -0.01                                                                              +0.01                                                                              0    -0.02                                                                              -0.02                                       a propionate                                                                  radical                                                             Example 59,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              0    -0.01                                                                              -0.02                                                                              -0.02                                       an acetate                                                                    radical                                                             Example 60,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              -0.01                                                                              0                                           a propionate                                                                  radical                                                             Example 61,                                                                             Compound having                                                                        -0.01                                                                              -0.03                                                                              +0.01                                                                              -0.02                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 62,                                                                             Compound having                                                                        -0.02                                                                              -0.01                                                                              +0.01                                                                              -0.02                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 63,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.03                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 64,                                                                             Compound having                                                                        -0.02                                                                              -0.01                                                                              +0.02                                                                              -0.03                                                                              -0.02                                                                              -0.02                                       an acetate                                                                    radical                                                             Example 65,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              0    -0.02                                                                              -0.02                                                                              -0.02                                       a propionate                                                                  radical                                                             Example 66,                                                                             Compound having                                                                        -0.01                                                                              -0.02                                                                              +0.02                                                                              -0.01                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 67,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.02                                                                              -0.01                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 68,                                                                             Compound having                                                                        -0.03                                                                              -0.03                                                                              +0.01                                                                              -0.01                                                                              0    -0.01                                       an acetate                                                                    radical                                                             Example 69,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.02                                                                              -0.02                                                                              -0.01                                                                              0                                           an acetate                                                                    radical                                                             Example 70,                                                                             Compound having                                                                        -0.02                                                                              -0.02                                                                              +0.01                                                                              -0.03                                                                              -0.02                                                                              -0.02                                       an acetate                                                                    radical                                                             Lauryldimethylbetaine                                                                            -0.10                                                                              -0.19                                                                              +0.09                                                                              -0.15                                                                              -0.23                                                                              -0.15                             1-Hydroxyethyl-2-unde-                                                                           -0.12                                                                              -0.16                                                                              +0.10                                                                              -0.12                                                                              -0.24                                                                              -0.12                             cylimidazolium betaine                                                        __________________________________________________________________________

INDUSTRIAL APPLICABILITY

Since the bactericidal surface active agents of this invention exhibitexcellent bactericidal action against any of the aerobic, anaerobic,gram-positive and gram-negative bacteria, they are of high industrialapplicability.

We claim:
 1. A cyclic amide compound of the formula ##STR86## wherein Ris an alkyl group, alkenyl group, monoalkylphenyl group, monoalkylbenzylgroup, hydroxyalkyl group, alkylcarbonyl group, alkenylcarbonyl orhydroxysubstituted alkyl- or alkenyl-carbonyl group having 8 to 22carbon atoms in total, R', R" and R"' are hydrogen atoms or methylgroups, A is hydrogen atom or methyl group, 0≦W≦1, 0≦X+Z≦3, 0≦Y≦3,0≦p+q+r≦3, m=1 or 2, and n=2 or 3; said compound may assume a structurein which, if necessary, the nitrogen atoms, except forthe amidegrouping, may combine with a carboxylate radical by covalent bond or toadd to a carboxylate.
 2. A compound according to claim 1, wherein thecyclic amide is4-dodecylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.
 3. Acompound according to claim 1, wherein the cyclic amide is4-dodecylaminoethylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.4. A compound according to claim 1, wherein the cyclic amide is4-tetradecylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.
 5. Acompound according to claim 1, wherein the cyclic amide is4-lauramidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.
 6. Acompound according to claim 1, wherein the cyclic amide is4-(2-hydroxyhexadecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.7. A compound according to claim 1, wherein the cyclic amide is4-tetradecylaminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.
 8. Acompound according to claim 1, wherein the cyclic amide is4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.9. A compound according to claim 1, wherein the cyclic amide is1-tetradecylaminoethyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.10. A compound according to claim 1, wherein the cyclic amide is1-(2-hydroxyhexadecyl)aminoethyl-3-methyl-3,6,7,8-tetrahydro-1,5-diazocin-2-one.11. A compound according to claim 1, wherein the cyclic amide is4-tetradecylaminoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.
 12. Acompound according to claim 1, wherein the cyclic amide is4-(2-hydroxyhexadecyl)aminoethyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.13. A compound according to claim 1, wherein the cyclic amide is4-tetradecylaminoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one.
 14. Acompound according to claim 1, wherein the cyclic amide is4-(2-hydroxyhexadecyl)aminoethyl-6,6-dimethyl-3-hydro-2H-1,4-diazepin-5-one.15. A compound according to claim 1, wherein the cyclic amide is1-tetradecylaminoethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-one.16. A compound according to claim 1, wherein the cyclic amide is1-(2-hydroxyhexadecyl)aminoethyl-3,3-dimethyl-6,7,8-trihydro-1,5-diazocin-5-one.17. A compound according to claim 1, wherein the cyclic amide is4-tetradecylaminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.18. A compound according to claim 1, wherein the cyclic amide is4-(2-hydroxyhexadecyl)aminoethyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one.19. A compound according to claim 1, wherein the cyclic amide is4-tetradecylaminoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.20. A compound according to claim 1, wherein the cyclic amide is4-lauramidoethyl-7-methyl-1-azonia-4-azacyclohept-7-en-5-one-1-acetate.21. An antibacterial surface active composition comprising water and anantibacterially effective amount of a cyclic amide compound inaccordance with claim 1.